Phenyl chloroformate → HCID 178521792, compound

HRID 476836Notes

Reaction equation

HRID 476836 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

N,N-dimethylacetamide (250 ml) was added to 36.6 g of 5-amino-2-mercaptobenzimidazole and 17.1 ml of pyridine, and 34.4 g of phenyl chloroformate was added dropwise at room temperature. The mixture was stirred at room temperature for 1.5 hours, and 1.5 liters of ice water was added. As a result, crystals precipitated. The resulting crystals were collected by filtration and recrystallized from acetonitrile to give 47.7 g of 2-mercapto-5-phenoxycarbonylaminobenzimidazole.

Workup

  1. additionwas added dropwise at room temperature
  2. customAs a result, crystals precipitated
  3. filtrationThe resulting crystals were collected by filtration
  4. customrecrystallized from acetonitrile

Sources & evidence

ORD record
ord-3ee287c9d22646e78ea4caf03965ea24
Source dataset
uspto-grants-1989_12
Patent number
US04886738

Reaction notes

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