SU1648949A1 - Method for obtaining 2,4,5-substituted 4n-1,3- thiadiazines - Google Patents
Method for obtaining 2,4,5-substituted 4n-1,3- thiadiazines Download PDFInfo
- Publication number
- SU1648949A1 SU1648949A1 SU894685327A SU4685327A SU1648949A1 SU 1648949 A1 SU1648949 A1 SU 1648949A1 SU 894685327 A SU894685327 A SU 894685327A SU 4685327 A SU4685327 A SU 4685327A SU 1648949 A1 SU1648949 A1 SU 1648949A1
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- SU
- USSR - Soviet Union
- Prior art keywords
- phenyl
- acetyl
- ethoxycarbonyl
- thiadiazines
- substituted
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 7
- -1 n-tolyl Chemical group 0.000 claims abstract description 12
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims abstract description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 9
- AVHCHJKMIGPLIZ-UHFFFAOYSA-N 4h-1,3,4-thiadiazine Chemical class N1C=CSC=N1 AVHCHJKMIGPLIZ-UHFFFAOYSA-N 0.000 claims abstract description 4
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims abstract description 3
- 229940072033 potash Drugs 0.000 claims abstract description 3
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims abstract description 3
- 235000015320 potassium carbonate Nutrition 0.000 claims abstract description 3
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 claims abstract description 3
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims abstract 4
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims abstract 4
- 239000003513 alkali Substances 0.000 claims abstract 2
- 125000000217 alkyl group Chemical group 0.000 claims abstract 2
- 239000003960 organic solvent Substances 0.000 claims abstract 2
- 239000002253 acid Substances 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 2
- 150000001875 compounds Chemical class 0.000 claims 2
- 229910052717 sulfur Inorganic materials 0.000 claims 2
- 239000011593 sulfur Substances 0.000 claims 2
- 230000003993 interaction Effects 0.000 claims 1
- 238000005282 brightening Methods 0.000 abstract description 2
- 239000003795 chemical substances by application Substances 0.000 abstract description 2
- 239000011810 insulating material Substances 0.000 abstract description 2
- 239000000463 material Substances 0.000 abstract description 2
- 238000002360 preparation method Methods 0.000 abstract description 2
- 239000011347 resin Substances 0.000 abstract description 2
- 229920005989 resin Polymers 0.000 abstract description 2
- 229920001187 thermosetting polymer Polymers 0.000 abstract description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 2
- 150000002391 heterocyclic compounds Chemical class 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 229960003424 phenylacetic acid Drugs 0.000 description 4
- 239000003279 phenylacetic acid Substances 0.000 description 4
- AUUTXOKCFQTKPL-UHFFFAOYSA-N 2-oxopropanoyl chloride Chemical compound CC(=O)C(Cl)=O AUUTXOKCFQTKPL-UHFFFAOYSA-N 0.000 description 3
- ZVVWZNFSMIFGEP-UHFFFAOYSA-N 2-(4-ethoxyphenyl)acetic acid Chemical compound CCOC1=CC=C(CC(O)=O)C=C1 ZVVWZNFSMIFGEP-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- AKPCOQJLPNEZOD-UHFFFAOYSA-N 2,4,5-triphenyl-1,3,4-thiadiazine Chemical compound S1C=C(C=2C=CC=CC=2)N(C=2C=CC=CC=2)N=C1C1=CC=CC=C1 AKPCOQJLPNEZOD-UHFFFAOYSA-N 0.000 description 1
- GXXXUZIRGXYDFP-UHFFFAOYSA-N 2-(4-methylphenyl)acetic acid Chemical compound CC1=CC=C(CC(O)=O)C=C1 GXXXUZIRGXYDFP-UHFFFAOYSA-N 0.000 description 1
- MOMFXATYAINJML-UHFFFAOYSA-N 2-Acetylthiazole Chemical group CC(=O)C1=NC=CS1 MOMFXATYAINJML-UHFFFAOYSA-N 0.000 description 1
- FPYUJUBAXZAQNL-UHFFFAOYSA-N 2-chlorobenzaldehyde Chemical compound ClC1=CC=CC=C1C=O FPYUJUBAXZAQNL-UHFFFAOYSA-N 0.000 description 1
- WLJVXDMOQOGPHL-PPJXEINESA-N 2-phenylacetic acid Chemical compound O[14C](=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-PPJXEINESA-N 0.000 description 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- PYAHDXYJSYTROA-UHFFFAOYSA-N [Cl].C(C(=O)C)(=O)O Chemical compound [Cl].C(C(=O)C)(=O)O PYAHDXYJSYTROA-UHFFFAOYSA-N 0.000 description 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 235000011089 carbon dioxide Nutrition 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 239000003792 electrolyte Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000002203 pretreatment Methods 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 150000008334 thiadiazines Chemical class 0.000 description 1
- 150000003556 thioamides Chemical class 0.000 description 1
Landscapes
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
Abstract
Изобретение относитс к гетероциклическим соединени м, в частности к получению 2,4.5-эамещенных 4Н-1,3,4-тиадиазинов ф-лы Ј-СН C(Ri)-N( C(R), где R ацетил , фенил, этоксикарбонил; RI -фенил, n-толил, п-бромфенил, n-этоксифенил, которые используют дл получени термореактивных смол и изолирующих материалов в фотографических материалах и в качестве блескообразующих добавок Цель - повышение выхода целевого продукта и упрощение технологии. Получение ведут реакцией соответствующего о. -хлоргидразона с диал- килтиоамидом арилуксусной кислоты ф-лы Rl-CH2C(S)-NR2, где RI - ацетил, фенил, этоксикарбонил; R2 - алкил, в среде инертного органического растворител при комнатной температуре в присутствии поташа или щелочи и бромистого тетрабутилам- мони . Выход 84-86%The invention relates to heterocyclic compounds, in particular to the preparation of 2,4.5-substituted 4H-1,3,4-thiadiazines in the form of Ј-CH C (Ri) -N (C (R), where R is acetyl, phenyl, ethoxycarbonyl ; RI is phenyl, n-tolyl, p-bromophenyl, n-ethoxyphenyl, which are used to obtain thermosetting resins and insulating materials in photographic materials and as brightening agents. The purpose is to increase the yield of the target product and simplify the technology. -chlorhydrazone with aryl acetic acid dialkiloamidom f-ly Rl-CH2C ( S) -NR2, where RI is acetyl, phenyl, ethoxycarbonyl; R2 is alkyl, in an inert organic solvent at room temperature in the presence of potash or alkali and tetrabutylammonium bromide. 84-86%
Description
Изобретение относитс к способу получени 2,4,5-замещенных 4Н-1,3,4-тиадиа- зинов общей формулыThe invention relates to a process for the preparation of 2,4,5-substituted 4H-1,3,4-thiadiazines of the general formula
PhPh
ii
R,R,
NN
ЧДBH
S К где R - ацетил, фенил, зтоксикарбонил;S K where R is acetyl, phenyl, ztoxycarbonyl;
RI - фенил, n-толил, п-бромфенил, п- этоксифенил.RI is phenyl, n-tolyl, p-bromophenyl, p-ethoxyphenyl.
Указанные производные тиадиазинов могут быть использованы дл получени термореактивных смол и изолирующих материалов в фотографических материалах дл повышени чувствительности в качестве блескообразующих добавок, позвол ющих повысить рассеивающую способность электролитов .These thiadiazine derivatives can be used to obtain thermosetting resins and insulating materials in photographic materials to increase sensitivity as brightening agents, which make it possible to increase the scattering ability of electrolytes.
Целью изобретени вл етс увеличение выхода целевых продуктов и упрощение технологии.The aim of the invention is to increase the yield of target products and simplify the technology.
Процесс проходит по следующей схеме сThe process is as follows:
RrCH2C;RrCH2C;
NR, NR,
K;C03(KOH iK; C03 (KOH i
WH Wh
6ns6ns
-R-CC1 N-NH-C6H5 CfiHs-R-CC1 N-NH-C6H5 CfiHs
P.ANP.AN
4s4s
П р и м е р 1 2-Ацетил-4,5-дифенил-4Н- 1,3,4-тиадиазинPRI me R 1 2-Acetyl-4,5-diphenyl-4H-1,3,4-thiadiazine
К раствору, содержащему 2,5 ммоль пентаметилентиоамида фенилуксусной кислоты и 0,2 г бромистого тетрабутиламмони в 5 мл бензола прибавл ют 1,0 г порошкообразного поташа или едкого кали и затем при комнатной температуре и интенсивном перемешивании прибавл ют в течение 30 мин в виде раствора в 5 мл бензола или в виде порошка 2,55 ммоль фенилгидразона хло- рангидрида пировиноградной кислоты и пеО1.0 g of powdered potash or potassium hydroxide was added to a solution containing 2.5 mmoles of pentamethylene thioamide of phenylacetic acid and 0.2 g of tetrabutylammonium bromide in 5 ml of benzene and then, at room temperature and vigorous stirring, added in the form of a solution in 5 ml of benzene or in the form of powder 2.55 mmol of phenylhydrazone of pyruvic acid chloride and peO
0000
юYu
чОcho
ремешивают 10 мин. Реакционную смесь фильтруют через ел ой силикагел и упаривают.stir 10 min. The reaction mixture was filtered through silica gel and evaporated.
Выход продукта 96%, т.пл. 144-145°С (из этанола).The product yield is 96%, so pl. 144-145 ° C (from ethanol).
Найдено, %: N 9,80; S 10,84.Found,%: N 9.80; S 10.84.
C17H14N2OSC17H14N2OS
Вычислено, %: N 9,25; S 10,89.Calculated,%: N 9.25; S 10.89.
П р и м е р 2. 2,4,5-Трифенил-4Н-1,3,4- тиадиазин.Example 2 2,4,5-Triphenyl-4H-1,3,4-thiadiazine.
Получают из пентаметилентиоамида фенилуксусной кислоты и фенилгидразона хлорбензальдегида аналогично примеру 1.Phenylacetic acid and phenylhydrazone chlorobenzaldehyde is obtained from pentamethylene thioamide in analogy to example 1.
Выход продукта 94%, т.пл. 199-20°С(из эталона), желтые иглы.The product yield is 94%, so pl. 199-20 ° C (from standard), yellow needles.
Найдено, %: N8,62; 39,55.Found,%: N8.62; 39.55.
C2lHi6N2SC2lHi6N2S
Вычислено, %: N 8,53; S 9,56.Calculated,%: N 8.53; S 9,56.
П р и м е р 3. 2-Этоксикарбонил-4,5-ди- фенил-4Н-1,3,4-тиадиазин.PRI me R 3. 2-Ethoxycarbonyl-4,5-diphenyl-4H-1,3,4-thiadiazine.
Получают из пентаметилентиоамида фенилуксусной кислоты и этилового эфира фенилгидразона хлорангидрида щавелевой кислоты аналогично примеру 1.Phenylacetic acid and phenylhydrazone of oxalic acid chloride are obtained from pentamethylene thioamide of phenylacetic acid, analogously to example 1.
Выход продукта 96%, красные иглы, из этанола, т.пл. 123-125°С.The yield of the product is 96%, red needles, from ethanol, so pl. 123-125 ° C.
Найдено, %: N 8,22; S 9,76.Found,%: N 8.22; S 9.76.
CigHisN202SCigHisN202S
Вычислено, %: N 8,28; S 9,47,Calculated,%: N 8.28; S 9.47,
П р и м е р 4. 2-Ацетил-4-п-бромфенил- 5-фенил-4Н-1,3,4-тиадиазин.PRI me R 4. 2-Acetyl-4-p-bromophenyl-5-phenyl-4H-1,3,4-thiadiazine.
Получают из N-морфолинотиоамида фенилуксусной кислоты и фенилгидразона хлорангидрида пировиноградной кислоты аналогично примеру 1.Prepared from phenyl acetic acid N-morpholinothioamide and phenylhydrazone of pyruvic acid chloride as in Example 1.
Выход 95%, красные иглы, т.пл 139- 140°С (из этанола).95% yield, red needles, mp: 139-140 ° C (from ethanol).
Вычислено, %: N 7,50; S 8,59.Calculated,%: N 7.50; S 8.59.
Ci7Hi3BrN2OSCi7Hi3BrN2OS
Найдено, %: N 7,52; S 8,27.Found,%: N 7.52; S 8.27.
П р и м е р 5. 2-Ацетил-4-п-толил-5-фе- нил-4Н-1,3,4-тиадиазин.EXAMPLE 5 2-Acetyl-4-p-tolyl-5-phenyl-4H-1,3,4-thiadiazine.
Получают из N-гморфолинотиоамида п- толилуксусной кислоты и фенилгидразона хлорзнгидрида пировиноградной кислоты аналогично примеру 1.Prepared from p-tolyl acetic acid N-Hmorpholinothioamide and phenylhydrazone pyruvic acid chlorine as in Example 1.
Выход 95%, красные иглы, т.пл, 125- 126°С (из этанола).95% yield, red needles, mp, 125- 126 ° C (from ethanol).
Найдено, %:N9,12;S 10,40,Found,%: N9,12; S 10,40,
Ci8Hi6N2OSCi8Hi6N2OS
Вычислено, %: N 9,08; S 10,40.Calculated,%: N 9.08; S 10.40.
Примерб. 2-Ацетил 4-п-зтоксифенил- 4Н-1,3,4-тиадиазин.Example 2-Acetyl 4-p-ztoxyphenyl-4H-1,3,4-thiadiazine.
Получают из N-морфолинотиоамида п- этоксифенилуксусной кислоты и фенилгидразона хлорангидрида пировиноградной кислоты аналогично примеру 1. Выход93%,красныеиглы,т.пл.133-134°С.Prepared from N-morpholinothioamide p-ethoxyphenylacetic acid and phenylhydrazone of pyruvic acid chloride as in Example 1. Yield 93%, red needles, mp. 133-134 ° C.
Найдено, %: N8,35; 59,63.Found,%: N8.35; 59.63.
CigHiaN202SCigHiaN202S
Вычислено, %: N 8,28; S 9,47.Calculated,%: N 8.28; S 9.47.
Таким образом, предлагаемый способ синтеза основываетс на легкодоступных и стабильных тиоамидах арилуксусных кислот . Используемые реагенты не требуют специальной предварительной очистки и обезвоживани . Использование предлагае- мого способа позвол ет отказатьс от применени специальных приспособлений, предохран ющих реакционную смесь от контакта с влагой и кислородом воздуха, отпадает необходимость применени инер- тных газов, например аргона, охлаждающих бань, содержащих жидкий азот или сухой лед. В результате реакции выдел ютс исключительно 2,4,5-замещенные 4Н-1,3,4-тиа- диазины со стабильными и высокими выходами (96% против84-86% по известному способу).Thus, the proposed synthesis method is based on readily available and stable arylacetic acid thioamides. The reagents used do not require special pre-treatment and dehydration. The use of the proposed method makes it possible to refuse the use of special devices that prevent the reaction mixture from contact with moisture and oxygen of the air; there is no need to use inertial gases, such as argon, cooling baths containing liquid nitrogen or dry ice. As a result of the reaction, only 2,4,5-substituted 4H-1,3,4-thiadiazines with stable and high yields (96% vs. 84-86% by a known method) are recovered.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SU894685327A SU1648949A1 (en) | 1989-04-25 | 1989-04-25 | Method for obtaining 2,4,5-substituted 4n-1,3- thiadiazines |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SU894685327A SU1648949A1 (en) | 1989-04-25 | 1989-04-25 | Method for obtaining 2,4,5-substituted 4n-1,3- thiadiazines |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU1648949A1 true SU1648949A1 (en) | 1991-05-15 |
Family
ID=21444759
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU894685327A SU1648949A1 (en) | 1989-04-25 | 1989-04-25 | Method for obtaining 2,4,5-substituted 4n-1,3- thiadiazines |
Country Status (1)
| Country | Link |
|---|---|
| SU (1) | SU1648949A1 (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2161613C2 (en) * | 1995-01-28 | 2001-01-10 | Мерк Патент Гмбх | Arylalkylthiadiazinones, method of their synthesis, pharmaceutical composition |
| RU2162087C2 (en) * | 1995-01-11 | 2001-01-20 | Мерк Патент Гмбх | 3-alkoxycarbonylthiadiazinones, method of their synthesis and pharmaceutical composition |
-
1989
- 1989-04-25 SU SU894685327A patent/SU1648949A1/en active
Non-Patent Citations (1)
| Title |
|---|
| Авторское свидетельство СССР № 537999, кл. С 07 D 285/16. ЖОРХ, 1981, т. 17, вып.1,с.2289-2294 * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2162087C2 (en) * | 1995-01-11 | 2001-01-20 | Мерк Патент Гмбх | 3-alkoxycarbonylthiadiazinones, method of their synthesis and pharmaceutical composition |
| RU2161613C2 (en) * | 1995-01-28 | 2001-01-10 | Мерк Патент Гмбх | Arylalkylthiadiazinones, method of their synthesis, pharmaceutical composition |
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