Chlorosuccinimide → HCID 53901979, compound

HRID 904826Notes

Reaction equation

HRID 904826 reaction equation
[CH:1]([S:4]([N:7]1[C:11]2[CH:12]=[C:13]([C:16](=[CH2:23])[C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH:14]=[CH:15][C:10]=2[N:9]=[C:8]1[NH2:24])(=[O:6])=[O:5])([CH3:3])[CH3:2].[Cl:25]N1C(=O)CCC1=O>O1CCCC1>[CH:1]([S:4]([N:7]1[C:11]2[CH:12]=[C:13]([C:16](=[CH:23][Cl:25])[C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH:14]=[CH:15][C:10]=2[N:9]=[C:8]1[NH2:24])(=[O:5])=[O:6])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 13345577HCID 13345577, compound

Product 1

HCID 53901979HCID 53901979, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 4.0 g. of 1-isopropylsulfonyl-2-amino-6-(α-methylenebenzyl)benzimidazole (from U.S. Pat. No. 4,118,742) in 100 ml. of tetrahydrofuran was added in one portion 1.56 g. of N-chlorosuccinimide. The reaction mixture was heated at reflux for two and one-half hours, and then cooled to room temperature. The reaction solvent was removed by evaporation under reduced pressure to provide the crude product as a gum. The gum was suspended in water, and then was extracted into chloroform. The chloroform extracts were combined, washed with fresh water, dried, and the solvent was removed by evaporation under reduced pressure. The product thus formed was dissolved in 50 ml. of diethyl ether, and after concentrating the volume of the mixture to about 25 ml., a white crystalline product precipitated and was identified as 1.5 g. of trans-1-isopropylsulfonyl-2-amino-6-(α-chloromethylenebenzyl)benzimidazole. M.P. 180°-181° C. Yield 34%.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for two and one-half hours
  3. customThe reaction solvent was removed by evaporation under reduced pressure

Sources & evidence

ORD record
ord-f3b03cd62fb442bd9aa269a752fef736
Source dataset
uspto-grants-1983_12
Patent number
US04420479

Reaction notes

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