Pyridine → HCID 178521792, compound

HRID 1031416Notes

Reaction equation

HRID 1031416 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.Cl[C:19]([O:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:20]>CN(C)C(=O)C>[SH:9][C:7]1[NH:8][C:4]2[CH:3]=[C:2]([NH:1][C:19]([O:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[O:20])[CH:11]=[CH:10][C:5]=2[N:6]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 15891Phenyl chloroformateHCID 178507340HCID 178507340, compound

Product 1

HCID 178521792HCID 178521792, compoundYield 76.1%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

36.6 g of 5-amino-2-mercaptobenzimidazole and 17.1 ml of pyridine were added to 250 ml of N,N-dimethylacetamide. 34.4 g of phenyl chloroformate was added dropwise to the admixture at room temperature. The admixture was then stirred at room temperature for 1.5 hours. The solution was added to 1.5 l of ice water. The resulting crystal was filtered off. The crystal was recrystallized from acetonitrile to obtain 47.7 g of 2-mercapto-5-phenoxycarbonylaminobenzimidazole.

Workup

  1. filtrationThe resulting crystal was filtered off
  2. customThe crystal was recrystallized from acetonitrile

Sources & evidence

ORD record
ord-edac9463b3c1422fb35ce99bee6ed578
Source dataset
uspto-grants-1990_09
Patent number
US04954427

Reaction notes

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