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

HRID 276048Notes

Reaction equation

HRID 276048 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-131f86b61e344451bb5e1e50cb18a203
Source dataset
uspto-grants-2002_03
Patent number
US06352985B1

Reaction notes

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