Phenyl chloroformate → HCID 178521792, compound

HRID 1709959Notes

Reaction equation

HRID 1709959 reaction equation
CN(C)C(=O)C.[NH2:7][C:8]1[CH:17]=[CH:16][C:11]2[N:12]=[C:13]([SH:15])[NH:14][C:10]=2[CH:9]=1.Cl[C:19]([O:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:20]>N1C=CC=CC=1>[SH:15][C:13]1[NH:14][C:10]2[CH:9]=[C:8]([NH:7][C:19]([O:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[O:20])[CH:17]=[CH:16][C:11]=2[N:12]=1

Participants

5

Reactant 3

HCID 15891Phenyl chloroformateHCID 31374DimethylacetamideHCID 178507340HCID 178507340, compound

Product 1

HCID 178521792HCID 178521792, compoundYield 76.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

250 ml of N,N-dimethylacetoamide was added to a mixture of 36.6 g of 5-amino-2-mercaptobenzoimidazole with 7.1 ml of pyridine, and 34.4 g phenyl chloroformate was then added dropwisely to the obtained mixture at room temperature. After the obtained mixture had been agitated at room temperature for 1.5 hours, the mixture was poured into 1.5 1 of ice water to separate crystals. The obtained crystals were filtered off and then recrysyallized from acetonitrile, to obtain 47.7 g of 2-mercapto-5-phenoxycarbonylaminobenzoimidazole.

Workup

  1. additionwas then added dropwisely to the obtained mixture at room temperature
  2. customto separate crystals
  3. filtrationThe obtained crystals were filtered off

Sources & evidence

ORD record
ord-1168f22e6db54af6820135a5536098b3
Source dataset
uspto-grants-1990_08
Patent number
US04952483

Reaction notes

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