Pyridine → HCID 178521792, compound

HRID 2106988Notes

Reaction equation

HRID 2106988 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][C:5]2[N:6]=[C:7]([SH:9])[NH:8][C:4]=2[CH:3]=1.N1C=CC=CC=1.CN(C)C(=O)C.Cl[C:25]([O:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:26]>O>[SH:9][C:7]1[NH:8][C:4]2[CH:3]=[C:2]([NH:1][C:25]([O:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)=[O:26])[CH:11]=[CH:10][C:5]=2[N:6]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 15891Phenyl chloroformateHCID 31374DimethylacetamideHCID 178507340HCID 178507340, compound

Product 1

HCID 178521792HCID 178521792, compoundYield 76.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

36.6 g of 5-amino-2-mercaptobenzimidazole and 17.1 g of pyridine were added to 250 ml of N,N-dimethylacetamide, and thereto was added dropwise 34.4 g of phenyl chloroformate at room temperature. After the resulting solution as such was stirred for 1.5 hours at room temperature, 1.5 liters of ice cooled water was added to deposit crystals, which were filtered off and recrystallized from acetonitrile, whereby 47.7 g of 2-mercapto-5-phenoxycarbonylaminobenzimidazole was obtained.

Workup

  1. additionwas added to deposit crystals, which
  2. filtrationwere filtered off
  3. customrecrystallized from acetonitrile

Sources & evidence

ORD record
ord-88b39b49c1504811837e9f9b79faa019
Source dataset
uspto-grants-1990_06
Patent number
US04933265

Reaction notes

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