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

HRID 1276909Notes

Reaction equation

HRID 1276909 reaction equation
C(Cl)(=O)C(Cl)=O.[C:7]([C:10]1[CH:11]=[CH:12][C:13]2[N:17]=[C:16]([CH3:18])[N:15]([CH2:19][C:20]3[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][C:21]=3[Cl:27])[C:14]=2[CH:28]=1)(O)=[O:8].[NH3:29]>CN(C)C=O.C(Cl)Cl>[C:7]([C:10]1[CH:11]=[CH:12][C:13]2[N:17]=[C:16]([CH3:18])[N:15]([CH2:19][C:20]3[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][C:21]=3[Cl:27])[C:14]=2[CH:28]=1)(=[O:8])[NH2:29]

Participants

6

Reactant 3

HCID 222AmmoniaHCID 65578Oxalyl chlorideHCID 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 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

Oxalyl chloride (0.437 g) was added to a solution of 0.490 g of 6-carboxy-1-(2,4-dichlorobenzyl)-2-methylbenzimidazole and 1 drop of N,N-dimethylformamide in 8 ml of methylene chloride while being cooled with ice, and the mixture was stirred at room temperature for 1.5 hours. Four milliliters of 28% aqueous ammonia were added thereto, and the solution was stirred at room temperature for 12 hours. The reaction solution was extracted with the addition of water and methylene chloride. The organic layer was concentrated, and the crystals precipitated were then collected, and were dried to give 0.240 g of 6-carbamoyl-1-(2,4-dichlorobenzyl)-2-methylbenzimidazole (223).

Workup

  1. temperaturewhile being cooled with ice
  2. stirringthe solution was stirred at room temperature for 12 hours
  3. extractionThe reaction solution was extracted with the addition of water and methylene chloride
  4. concentrationThe organic layer was concentrated
  5. customthe crystals precipitated
  6. customwere then collected
  7. customwere dried

Sources & evidence

ORD record
ord-4bc3a84e53274b2ebf86d85be77325bb
Source dataset
uspto-grants-2000_12
Patent number
US06166219

Reaction notes

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