SU448647A3 - Method of producing quinazolone diurethanes - Google Patents

Description

(54) METHOD OF OBTAINING HINAZOLONE DIURETHANES

(Iii) is not used as a solvent, then on

1 mol of the compound of the formula (II) are preferably introduced by I-10 mol, preferably 2.2-6 mol, of the compound of the formula (III).

If the hydroxyl compound is at the same time a solvent, it is recommended to add a small amount (0.1-5% by weight of the initial mixture) of the basic catalyst, for example triethylamine, pyridine, triethylenediamine or dimethylcyclohexylamine.

Example 1. (methoxycarbonylamino) -phenyl-3-phenyl-6-methoxycarbonylamino-4- (ZN) -quinazolone.

A mixture of 38 wt. including 2- (3-isocyanatophenyl) 3-phenyl - 6-isocyanato - 4- (3N) -quinazolone,

2ob. including triethylamine and 200 vol. including methanol is heated to boiling for 30 minutes. Then the reaction mass is mixed with water and the separated product is recrystallized from ethanol. Exit 36 weight. h. (81% of theory); m.p. 243-245 ° C.

Found,%: C 64.7; H 4.7; O 18.2; N 12.8.

Calculated,%: C 64.86; H 4.54; O 18.0; N 12.61.

Example 2-13. Analogously to example 1, from the corresponding diisocyanate and alcohol get the quinazolone diurethanes, presented in table. one.

Example 14. (p, 7-dioxypropyloxycarbonylamino) -phenyl-3-phenyl-6- (p, 7-dioxypropyloxycarbonylamino) -4- (3N) -quinazolone.

13 wt. including 2- (3-isocyanatophenyl) -3-phenyl-6-isocyanato-4- (3N) -quinazolone is dissolved in 60 vol. including dimethylformamide. Then add 60 wt. including glycerin, dissolved in 60 vol. including anhydrous dimethylformamide, and 5 about. including triethylamine. Then extra

stirred for 1 hour at room temperature and 4 hours at 60 ° C, the mixture was poured into water, the precipitate was filtered off with suction and dried. Output 15 wt. h. (67% of theory); m.p. 172-174 ° C. Found,%: C 59.1; H 5.1; About 24.9; N 10.0.

Calculated,%: C 59.6; H 4.96; O 25.55; N 9.95.

According to NMR spectroscopy obtained

the product contains only small amounts of isomeric (bisoxymethylmethoxycarbonylamino) -phenyl - 3-phenyl-6 - (bismethylmethoxycarbonylamino) -4- (3N) -quinazolone.

Example 15. (methoxythiocarbonylamino) -phenyl-3-phenyl-6-methoxythiocarbonylamino-4- (3H) -quinazolone.

5 wt. including sodium metal is dissolved in 150 vol. including absolute methanol. Then add 34 weight. including 2- (3-isothiocyanatophenyl) 2-phenyl-6-isothiocyanato-4- (3N) -quinazolone and further stirred for 1.5 hours at room temperature (20 ° C) and 1 hour at 40 ° C. The solution is sucked off and a small amount of insoluble precipitate is removed. Water is added to the filtrate and acidified with hydrochloric acid. The precipitate is filtered off with suction and dried at 50 ° C under vacuum.

The yield of the target product is 30.5 wt. h (78% of theory); m.p. 155-158 ° C.

Found,%: C 60.1; H 4.5; O 10.4; N 12.0; S 13.0.

Calculated,%: C 60.5; H 4.2; O 10.1; N 11.75; S 13.4.

Example 16-17. Analogously to example 15

from 2- (3-isothio anato) -3-phenyl-6-isothiocyanato-4- (3N) -quinazolone and the corresponding

sodium alcohols get indicated in

Table 2 dithiourenates hinazolona.

Table 1

 i lOl

CH.-CH-O-C-NH-V

II p

about 1 /

x / - (/ / 4 /

CH.-CH.-O-C-MiY Y

-W

h {)

about {U e

N / M BUT - SI IX on-sn.go-e No. 1, o Rl /

shhh 1 I

NgC CH-CHf-O (Shg and-C ShIII f-. O.

79

108-112

01,

, -NH-C-0-CH2-OH, -N UI Shz

,

C. | 0,

126-129

64

./C-.Nt

MN-s-o-OHvr he 2-N Oznu O. T-C-099

189-200

n., s-w .. I I

with - about - OI, - CH Sho

d ./

about

0 -NH-C- (ONCO HC-CH 127-130 CH2-C JCH 155-157

0-0-NH II

about

99

145-15 (

v -NH --- - 45O

and

,WITH

 /.

CH-Mr.-W.-0-C-NH II O

j

f-CH-CH. rO-C-H-t V

..with

about

Continuation

90-95

84

-Sh-С-О-СНгСНг-оХ О,

1Q

50

161-164

- Shh-o - Sh.-Shg

, Sn.o-with-sh-.

N N-CH10 about 1 Ul / s

175-178

96

x

, NH-C-0-CH./-OH2-N Ы

ABOUT

 about

about II

|

.r-CH.O-r-NU- / V CH -1

About ..v-h / kg ush-s-0-sno-ch, -N

Yu N-CHrCHrO-C-NliY Y N Nо L HSGC K-I-cn2-cc-o-e-ct {W L.j- /, / w with 171-174

87

/ ABOUT

146-150

95

160-165

74 y,

Example

H5S-1SH2) gO-S-M1- | Y s

-N YoY r С-Ш -СНг-СНг-0-С-Ш

Subject invention

Claims (3)

1. A method for producing quinazolone diurethanas of the general formula ABOUT H / BO-0-Sh-4O X. „, Ok V i where X is oxygen or sulfur; R is alkyl (may be substituted by dialkylamino, furyl, tetrahydrofuryl, pyrrolidinyl, piperidyl, hexahydroazepinyl, imidazolyl, triazolyl, or one or more hydroxyl groups) or cycloalkyl (may be substituted by alkyl), R is alkyl or phenyl (may be substituted by alkyl, alkoxy or halogen), Output, % T. pl. Formula - / from theory 72.5 91-93 ib 128-136 87 characterized in that diisocyanates or dithioisocyanates of the general formula .XCN NCX (C) ten where X and R have the indicated meanings, are reacted with alcohols of the general formula R-OH (III) where R has the indicated meanings. 2. A method according to claim 1, characterized in that the reaction is carried out at 10-120 ° C. 3. Method according to paragraphs. 1 and 2, characterized in that the process is carried out in the presence of an inert solvent. ,