SU333837A1 - Process for preparing derivatives of 2-animosenseimidazole - Google Patents

Abstract

The method of obtaining 2-aminobenzimidazOl derivatives of the general formula .NC-NH-X, where X and Y are hydrogen, the groups are COOR, or are CONHRj, in which 1 R and R (are alkyl, aryl, acyl; Z is hydrogen, alkyl, halogen , alkoxy or nitro group, by reacting the corresponding isocyanate with 2-aminobenzimidazole or its derivative in an organic solvent medium, followed by isolating the target product with known techniques, characterized in that, in order to simplify the process, increase the yield and purity of the target product, the process is in hydrocarbon solvent.

Description

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The invention relates to the field of the production of compounds that can be used in agriculture. The known method is to obtain alkyl 2 -benzimidazolylureas by reacting the corresponding isocyanate and 2-aminobenzimidazole in plant. pyridine thief with D11it; flax heating. In order to simplify the process, increase the yield and purity of the target product, a method is proposed for obtaining 2-aminobenzimidazole derivatives of the general formula C-NH-X where X and Y are hydrogen, the groups are COOR or are CONHR, in which R and R are alkyl, aryl, acyl; Z is hydrogen, alkyl, halogen alkoxy or nitro, by reacting the corresponding iso, cyanate with 2-aminobenzimidazole in an inert organic suspension (solvent, for example benzene, then luol, isooctane, etc., at room temperature. Except The proposed method, due to the elimination of the stage, the solution of the starting materials in pyridine with the subsequent separation of the target product by dilution with water, allows to obtain a final product of high purity in a quantitative yield — and does not require special purification. from waters. PRI and .MER 1. 2-Amino-1- (H-pbutylcarbamoyl) -benzimidazole. To a suspension of 3.72 g of 2-aminobenzim dazol in 40 ml of dry benzene is added 2.77 g of p- butyl isocyanate. After stirring for 2 hours, the precipitate formed is filtered off, washed with acetone, dried in air and 6.35 g of 2-amino-1- (Npbuty-carbamoyl) -benzimidazole are obtained, melting 72 Calculated,% 62.01; H 6.90; N 24.18. Example 2. 1- (2-Benzimidazolyl) -3-p-butylurea. 0.72 g of 2-amino-1- (H-p-butylcarbamoyl) -benzimidazole in 2 ml of isooctane, heat for 0.5 h in a water bath. After cooling, the precipitate is filtered, washed with isooctane, dried in air, and 0.27 g of 1- (2-benzimidazolyl) -3-p-butyl urea is obtained, melting with decomposition at. Found,%: N 24.37; 24.28. C, H, 5N40. Calculated,%: N 24,18. Example 3. Methyl-N- 2- (1-pbutylcarbamoyl) benzimidazolyl-carbamate. . 0.85 g of p-butyl isocyanate is added to a suspension of 1.64 g of methyl M-2- (benzimidazolyl) carbamate. After 2 hours of stirring, a white precipitate is filtered off, washed with benzene, dried in air, and 2.49 g of methyl N-L2- (1-p-butylcarbamoyl) -benzimidazolyl-carbamate, melting with decomposition, is obtained. Found,%: C 57.80; 58.17; H 6.50; 6.57; N 19.51; 19.41. . Calculated,%: C 57.98; H 6.21; N 19.30. Example 4. (1-carbomethoxy) -benzimidazolyl-3-p-butylurea. 0.22 g of p-butyl isocyanate is poured into a suspension of 0.43 g of methyl 2-amino-1-benzimidazolylcarbonate, in 20 ml of dry benzene. The resulting clear solution is stirred for 2 hours, then the benzene is evaporated and 5 ml of ether are added to the resulting viscous product. The white precipitate is filtered off, washed with ether, dried in air, and 0.65 g of 1-L2- (1-canopy) -benzimidazolyl-3-p-ftiylpurer melting with decomposition at 135 ° C is obtained. Found,%: N 19.25; 19.20. , Calculated,%: N 19.30. Example 5, 1-2- (benzimidazolyl) -3-phenylurea. 3 isocyanate. The mixture is heated for 1 hour in a water bath. The white amorphous precipitate formed is phy; washed, washed with acetone, dried in air, and 1.80 g (97%); 1- (2-benzimidaz6lyl) -3-phenylurea with m.p. 315 ° C (with decomposition). Found,%: N 22,58; 22.70. . Calculated,%: N 22,67. Example 6. 1- (2-Benzimidazole 3-benzoylurea) 0.36 g of benzoyl isocyanate are poured into a suspension of 0.33 g of 2-aminobenzimy dazol in 20 ml of dry benzene. After 2 hours of stirring, the precipitated white amorphous precipitate is filtered, washed with acetone, dried 0.67 g (97%) of 1- (2-benzimidaz6lyl) -3-benzoyl urea is obtained on air, which melts with decomposition at 280% C, 64.23; 63.03; H 4, 4 , 70; N 20.15; 20.41.,. Calculated,%: C 64.30; H 4.29; N 20.00. Example 7. (1-carbox-mimetic) -benzimidazolyl | -3- (4- chlorobenzoyl) urea. To a suspension of 1.8 g of methyl ester 2-amino-1-benzimidazolylcarbamine succinic acid lots in 20 ml of dry benzene poured 1.7 g of chlorobenzoyl isocyanate in 5 ml of dry benzene. After 2 stirring, the precipitated linen was filtered off, washed with benzene, dried, and I obtained 3.2 g (0.1%) (1-carbomethoxy) benzimidazolyl - 3- (4-chlorobenzoyl) urea with a mp of 165 C. Found:% C 54.45; 54.05; H 3.97; 3.86; N 15.01; 14.98; C1 10, 11; 9.87. 7. Calculated,%: C, 54.70; H 3.49; N 15.05; B1 9.55. f Example 8. 1- (2-Chlorophenylcarbaminoyl) -benzimidazolyl J 3- (2-chlorophenyl) -urea. 2.3 g of O-chlorophenyl isocyanate are added to a suspension of 1 g of 2-aminobenzimidazole in 50 ml of dry benzene. After 2 hours of stirring, a white precipitate is filtered off, washed with acetone, dried in air, and 3.22 g (98%) of (2-chlorophenylcarbaminoyl) benzimidazolyl-3- (2 chlorophenyl) urea, melting with decomposition at 298-300 ° C, is obtained. Found,%: C 57.08; 57.12; H 3.90; 4.00; N 15.58; 15.80; C1 16.23; 15.96. . Calculated,%: C 57.20; H 3.41; N 15.89; C1 16.12. Example 9. 1- {2- 1- (4-Chlorophenylcarbaminoyl) -benzimidazolyl-3- (2-chlorophenyl) -urea. 0.53 g of O-chlorophenyl isocyanate are added to a suspension of 1 g of 2-amino-1- N- (4 chlorophenyl) -carbaminoylT-benzimidazole in 30 ml of dry benzene. After 2 hours of stirring, the precipitate is filtered, washed with benzene, dried in air, and 1.43 g (94%) of 1- | 2- 1- (4-chlorophenylcarbaminoyl) -benzimidazolyl-3- (2-chlorophenyl) urea are obtained, melting with decomposition at 320 ° C. Found,%: N 16.08; 16.11. Ci, H, jCl2NyO. Calculated,%: N 15.90. Other examples of similarly semi-free compounds are listed in the table.

carbamoyl) -benzimidazole

95 92 (PL 29.36 29.50 with decomp.) 12 2-amino-1- (K-2-chlorophenylcarbamdyl) benz98 NMidazole 13 2-amino-1- (K-3-chlorophenylcarbamoyl) benz97 imidazole 14 2-amino-1- (L-4-chlorophenylcarbamoyl) benz98 imidazole 15 1- (2-benzimidazolyl) amount-3-methyl urea 16 Methyl-N-2- (1-phenyl-carbamoyl) benzimide 93 azolyl carbammate 171- ( 2-benzimidazolyl) -3- (2 chlorophenyl) 98: urea. 18 1- (2-benzimidazolyl) -3- (3-chlorophenyl) 97 urea 19 1- (2-benzimidazolsh1) -3- (4-chlorophenyl) 98 urea

20 1- (2-benzimnpazolyl) -3- (4-chlorobenzonl) 87 urea 21 1- (2-benzimidazolsh1) -3- (4-nitrophenoxy) 94 acetyl) -f urea

22 (1-carbrmethoxy) -benzimidaeol -3-phenylurea

Continuation, tables 260 C1 11,15 С С111,28

(10.85

320) (pl. 19.72 СН, 19.55 at once). 19.50 300 (pl. 19.68 19.55 s dec.) 19.71 310 (square 19.70 19.55 s. .) 19.53 320 (pl. 29.36 C H, 29.50 s dec.) 29.30 260 (pl. 18.41 18.35 s dec.) 18.32 320 19.72 19.55 ( 19.35 19.55 (decomp.) 19.56 310 19.70 C, 19.65 (19.53) 245 19.66, 19.43 (19, 50%) 23 (1-N-butylcarbaminoyl) -benzimidazolyl -3- (4-chlorophenyl) urea98 240

24 (4-chlorophenylcarbaminoyl) -benzimide 3 olyl 1-3-N-butylurea90 255

25 (1-methylcarbaminoyl) -benzimidazolyl-3-methyl urea 94

26 (1-PhenylcarbaminebenzimidazolylT-3-methylurea95

27 (2-chlorophenylcarbaminoyl) -benzimidazolyl | -3- (4-chlorophenyl) urea .94

281 -2- l- (2-chlorophenylcarbaminoyl) -benzimidazolyl -3- (4-chloroben3oyl) -urea 333837 з1 1П 4

18.00 ClNjO. 18.18 17.82

28,34

28.62

28.74

.jNjOi 23,0123, 28 23,32

15.89, Cj, H ,, 5Cl, jN502l5.90 15.60

14.94 C4jH, 5Cl2NjOj14.98

190

I I / L, .-,., Continuation of table 1 5 C. N 20 ClNjOj 18,18

Claims (1)

A method of obtaining derivatives of 2-aminobenzimidazole of the general formula z-h I C-NH-X. I Y where X and Y are hydrogen, the groups are COOR, or CONHRj in which; R and R ₍ are alkyl, aryl, acyl; Z is hydrogen, alkyl, halogen, alkoxy or nitro, by reacting the corresponding isocyanate with 2-aminobenzimidazole or its derivative in an organic solvent, followed by isolation of the target product by known methods, characterized in that, in order to simplify the process, increase the yield and purity of the target product, the process is carried out in a hydrocarbon solvent.