Ammonia → 6-Carbamoyl-1-(2,4-dichlorobenzyl)-2-methylbenzimidazole

HRID 1699619Notes

Reaction equation

HRID 1699619 reaction equation
[Cl-].[C:2]([C:5]1[CH:6]=[CH:7][C:8]2[N:12]=[C:11]([CH3:13])[N:10]([CH2:14][C:15]3[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=3[Cl:22])[C:9]=2[CH:23]=1)(O)=[O:3].[NH3:24]>CN(C)C=O.C(Cl)Cl.O>[C:2]([C:5]1[CH:6]=[CH:7][C:8]2[N:12]=[C:11]([CH3:13])[N:10]([CH2:14][C:15]3[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=3[Cl:22])[C:9]=2[CH:23]=1)(=[O:3])[NH2:24]

Participants

7

Reactant 3

HCID 222AmmoniaHCID 312ChlorideHCID 225088211-(2,4-Dichlorobenzyl)-2-methyl-1H-benzo[d]imidazole-6-carboxylic acid

Product 1

HCID 186811186-Carbamoyl-1-(2,4-dichlorobenzyl)-2-methylbenzimidazole

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

Oxylyl chloride (0.437 g) is added to a methylene chloride (8 ml) solution of 6-carboxy-1-(2,4-dichlorobenzyl)-2-methylbenzimidazole (0.490 g) and N,N-dimethylformamide (1 drop) under ice-chilled conditions, and the solution is stirred for 1.5 hours at room temperature. Then, 28% aqueous ammonia (4 ml) is added and the solution is stirred for 12 hours at room temperature. Water and methylene chloride are added to the reaction solution for extraction. After the organic layer is concentrated, precipitated crystals are collected, dried and 6-carbamoyl-1-(2,4-dichlorobenzyl)-2-methylbenzimidazole (0.240 g) is obtained. 1H-NMR (DMSO-d6, δ): 2.48 (3H, s), 5.54 (2H, s), 6.41 (1H, d, J=8.4 Hz), 7.21-8.02 (3H, m), 7.31 (1H, dd, J=2.2 and 8.4 Hz), 7.60 (1H, d, J=8.4 Hz), 7.75 (1H, m), 7.93 (1H, s).

Workup

  1. temperaturechilled conditions
  2. stirringthe solution is stirred for 12 hours at room temperature
  3. concentrationAfter the organic layer is concentrated
  4. customprecipitated crystals
  5. customare collected
  6. customdried

Sources & evidence

ORD record
ord-ac6e3d888c8c449bb604348bde1839de
Source dataset
uspto-grants-2002_02
Patent number
US06348032B1

Reaction notes

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