Acetic Acid → HCID 19858110, compound

HRID 2073231Notes

Reaction equation

HRID 2073231 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][C:3]=1[S:11](=[O:14])(=[O:13])[NH2:12].[NH2:15][N:16]1[C:20]2[CH:21]=[CH:22][C:23]([C:25]([O:27][CH3:28])=[O:26])=[CH:24][C:19]=2[NH:18][C:17]1=[S:29].C(O)(=O)C>CN(C)C=O.C(N(CC)CC)C.O>[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH:15][N:16]2[C:20]3[CH:21]=[CH:22][C:23]([C:25]([O:27][CH3:28])=[O:26])=[CH:24][C:19]=3[NH:18][C:17]2=[S:29])=[O:7])=[CH:4][C:3]=1[S:11](=[O:14])(=[O:13])[NH2:12]

Participants

7

Reactant 3

HCID 176Acetic Acid2×HCID 30179793-(Aminosulfonyl)-4-chlorobenzoyl chlorideHCID 19858102HCID 19858102, compound

Product 1

HCID 19858110HCID 19858110, compoundYield 55.2%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

2.54 g of 4-chloro-3-sulfamoylbenzoyl chloride were added in little portions to the solution of 2.2 g of 1-amino-5-methoxycarbonylbenzimidazole-2-thione in 8 ml of dimethylformamide and 1.4 ml of triethylamine while stirring. The reaction mixture was set aside overnight, then the pH value was adjusted to 5 by acetic acid and it was diluted with 100 ml of water. The separated gum slowly disaggregated to a powder which was filtered by suction, washed with water and dried at 80° C. The crude product obtained was boiled with 10 ml of glacial acetic acid for 30 minutes, then poured into 50 ml of water. The separated gum disaggregated to a powder by stirring. The precipitate was filtered by suction, washed with water and dried at 80° C. to give 2.4 g (54.5%) of 1-(4'-chloro-3'-sulfamoylbenzoyl)amino-5-methoxycarbonylbenzimidazole-2-thione, as a beige powder, m.p.: 258°-261° C. (with decomposition) after recrystallization from a mixture of dimethylformamide and water (1:2).

Workup

  1. filtrationwas filtered by suction
  2. washwashed with water
  3. customdried at 80° C
  4. customThe crude product obtained
  5. stirringby stirring
  6. filtrationThe precipitate was filtered by suction
  7. washwashed with water
  8. customdried at 80° C.

Sources & evidence

ORD record
ord-4a31ca967056488ead3123f9a4faef8e
Source dataset
uspto-grants-1990_04
Patent number
US04916149

Reaction notes

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