Diphenyl carbonate → 2-Aminobenzimidazole

HRID 2399025Notes

Reaction equation

HRID 2399025 reaction equation
[N:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[NH:3][C:2]=1[NH:10][C:11]([NH:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])=[O:12].[C:28]1([O:34]C(=O)OC2C=CC=CC=2)C=CC=CC=1>C1(C)C(C)=CC=CC=1>[N:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[NH:3][C:2]=1[NH:10][C:11]([NH:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])=[O:12].[NH2:10][C:2]1[NH:1][C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=1.[CH2:14]([N:13]=[C:11]=[O:12])[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27].[CH:14]1([N:13]2[C:28](=[O:34])[N:1]3[C:2](=[N:3][C:4]4[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=43)[NH:10][C:11]2=[O:12])[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]1

Participants

7

Reactant 2

HCID 7597Diphenyl carbonateHCID 21432568HCID 21432568, compound

Product 4

HCID 136242-AminobenzimidazoleHCID 3485710Tetradecyl isocyanateHCID 21432568HCID 21432568, compoundHCID 136053472HCID 136053472, compound

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

Melting point 100° C., with decomposition. IR(CHCl3) 1,562, 1,580, 1,602, 1,618, 1,665 and 1,725 cm-1. ##STR91## The starting material 3-methyl-2,4-dioxo-1,2,3,4-tetrahydro-s-triazino-[1,2-a]-benzimidazole is known from German Published Specification DOS 2,144,505 ##STR92## The starting material 3-phenyl-2,4-dioxo-1,2,3,4-tetrahydro-s-triazino-[1,2-a]-benzimidazole is known from German Published Specification DOS 2,144,505. ##STR93## The starting material 3-tetradecyl-2,4-dioxo-1,2,3,4-tetrahydro-s-triazino-[1,2-a]-benzimidazol (m.p. 193° C.) is obtained by reacting 1 -(benzimidazole-2-yl)-3-tetradecylurea and diphenylcarbonate. 1-(benzimidazole-2-yl)-3-tetradecylurea is formed by the reaction of 2-aminobenzimidazole and tetradecylisocyanate in xylene at 120° C. ##STR94## The starting material 3-cyclohexyl-2,4-dioxo-1,2,3,4-tetrahydro-s-triazino[1,2-a]-benzimidazole (m.p. 335° C.) is obtained from 1-(benzimidazole-2-yl)-3-cyclohexylurea and diphenylcarbonate. 1-(benzimidazole-2-yl)-3-cyclohexylurea is obtained from 2-aminobenzimidazole and cyclohexylisocyanate at about 120° C. in xylene. ##STR95## The starting material 3-(2-phenylethyl)-2,4-dioxo-1,2,3,4-tetrahydro-s-triazino-[1,2-a]-benzimidazole (m.p. 298° C.) is produced from diphenylcarbobate and 1-(benzimidazole-2-yl)-3-(2-phenylethyl)-urea. The latter is produced from N-benzimidazole-2-yl-carbamic acid phenyl ester and 2-phenylethylamine. ##STR96## The starting material 3-(ω-methylamino-carbonylpentyl)-2,4-dioxo-1,2,3,4-tetrahydro-s-triazino-[1,2-a]-benzimidazole (m.p. 268° C. destr.) is formed by boiling 3-(ω-methoxycarbonylpentyl)-2,4-dioxo-1,2,3,4-tetrahydro-s-triazino-[1,2-a]-benzimidazole (m.p. 221° C.) in a mixture of butanol and water with methylamine.

Sources & evidence

ORD record
ord-04f7774c243447c2b3339c0d271329ae
Source dataset
uspto-grants-1977_05
Patent number
US04026934

Reaction notes

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