HCID 19858089, compound → HCID 19858104, compound

HRID 2073234Notes

Reaction equation

HRID 2073234 reaction equation
[Cl:1][C:2]1[CH:27]=[CH:26][C:5]([C:6]([NH:8][N:9]2[C:13]3[CH:14]=[CH:15][C:16]([C:18]([O:20]C)=[O:19])=[CH:17][C:12]=3[N:11]=[C:10]2[S:22]([CH3:25])(=[O:24])=[O:23])=[O:7])=[CH:4][C:3]=1[S:28](=[O:31])(=[O:30])[NH2:29]>[OH-].[Na+]>[C:18]([C:16]1[CH:15]=[CH:14][C:13]2[N:9]([NH:8][C:6](=[O:7])[C:5]3[CH:26]=[CH:27][C:2]([Cl:1])=[C:3]([S:28](=[O:30])(=[O:31])[NH2:29])[CH:4]=3)[C:10]([S:22]([CH3:25])(=[O:23])=[O:24])=[N:11][C:12]=2[CH:17]=1)([OH:20])=[O:19]

Participants

3

Reactant 1

HCID 19858089HCID 19858089, compound

Product 1

HCID 19858104HCID 19858104, compoundYield 85.7%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Conditions

Temperature
50 °C

Procedure

A suspension containing 5.4 g of 1-(4'-chloro-3'-sulfamoylbenzoyl)amino-5-methoxycarbonyl-2-methylsulfonylbenzimidazole in 30 ml of 2N sodium hydroxide solution was stirred at 50° C. for 4 hours to give a clear violet solution which was clarified by activated carbon, filtered and the filtrate was acidified to pH 2 by adding 2N hydrochloric acid. The white precipitate was filtered by suction, washed with water and dried to give 4.43 g (85.7%) of 5-carboxy-1-(4'-chloro-3'-sulfamoylbenzoyl)amino-2-methylsulfonylbenzimidazole, as a white powdery solid, m.p.: 222°-225° C. (with decomposition) which is not changed after recrystallization from a mixture of dimethylformamide and water (3:2).

Workup

  1. customto give a clear violet solution which
  2. filtrationfiltered
  3. additionby adding 2N hydrochloric acid
  4. filtrationThe white precipitate was filtered by suction
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-e144f2473fd8468b969121cf0ce6dd4e
Source dataset
uspto-grants-1990_04
Patent number
US04916149

Reaction notes

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