GB133108A - - Google Patents
Info
- Publication number
- GB133108A GB133108A GB133108DA GB133108A GB 133108 A GB133108 A GB 133108A GB 133108D A GB133108D A GB 133108DA GB 133108 A GB133108 A GB 133108A
- Authority
- GB
- United Kingdom
- Prior art keywords
- aniline
- prepared
- hydrochloric acid
- condensing
- ordiethylaniline
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 abstract 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 5
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 abstract 2
- -1 may be present Chemical compound 0.000 abstract 2
- 238000000034 method Methods 0.000 abstract 2
- RZXMPPFPUUCRFN-UHFFFAOYSA-N p-toluidine Chemical compound CC1=CC=C(N)C=C1 RZXMPPFPUUCRFN-UHFFFAOYSA-N 0.000 abstract 2
- SSZWWUDQMAHNAQ-UHFFFAOYSA-N 3-chloropropane-1,2-diol Chemical compound OCC(O)CCl SSZWWUDQMAHNAQ-UHFFFAOYSA-N 0.000 abstract 1
- CCVPGTPQGAPAED-UHFFFAOYSA-N 3-nitro-4-phenylthiomorpholine Chemical compound [N+](=O)([O-])C1N(CCSC1)C1=CC=CC=C1 CCVPGTPQGAPAED-UHFFFAOYSA-N 0.000 abstract 1
- XJCVRTZCHMZPBD-UHFFFAOYSA-N 3-nitroaniline Chemical compound NC1=CC=CC([N+]([O-])=O)=C1 XJCVRTZCHMZPBD-UHFFFAOYSA-N 0.000 abstract 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 abstract 1
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methyl-N-phenylamine Natural products CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 abstract 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 238000009833 condensation Methods 0.000 abstract 1
- 230000005494 condensation Effects 0.000 abstract 1
- 229910052802 copper Inorganic materials 0.000 abstract 1
- 239000010949 copper Substances 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 abstract 1
- 230000003472 neutralizing effect Effects 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 150000003142 primary aromatic amines Chemical class 0.000 abstract 1
- GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/02—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements
- C07D295/027—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements containing only one hetero ring
- C07D295/033—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements containing only one hetero ring with the ring nitrogen atoms directly attached to carbocyclic rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
133,108. Robinson, R., Kay, F. W., and British Dyes, Ltd. June 26, 1918. N-Arylthiomorpholines are prepared by condensing primary aromatic amines having a free o - position with #-#<1>-dichlordiethylsulphide, in the presence or absence of solvents; substances neutralizing hydrochloric acid, e.g. soda, may be present, and copper may be added as a catalyst. According to examples, products are obtained from aniline, p-toluidine, m-nitraniline, and #- naphthylamine; the m-nitrophenylthiomorpholine may be reduced to the corresponding amino compound by the usual methods. Alternative methods of preparation are by heating aniline and its hydrochloride with #-#<1>-dioxydiethylsulphide, or by condensation of #-#<1>-dichlordietbylaniline with sodium sulphide. #-#<1>-Dich ordiethylaniline is prepared bv condensing aniline with glycol chlorhydrin and treating the resulting #-#<1>-dioxydiethylaniline with fuming hydrochloric acid.
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB133108A true GB133108A (en) |
Family
ID=1726555
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB133108D Active GB133108A (en) |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB133108A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2439749A (en) * | 1945-05-03 | 1948-04-13 | Joseph B Niederl | Nu-alkyl thiamorpholines and derivatives |
| US2692879A (en) * | 1950-11-03 | 1954-10-26 | Atlas Powder Co | Method of preparing n-substituted morpholines |
-
0
- GB GB133108D patent/GB133108A/en active Active
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2439749A (en) * | 1945-05-03 | 1948-04-13 | Joseph B Niederl | Nu-alkyl thiamorpholines and derivatives |
| US2692879A (en) * | 1950-11-03 | 1954-10-26 | Atlas Powder Co | Method of preparing n-substituted morpholines |
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