2-Bromopropane → HCID 53771469, compound

HRID 2053376Notes

Reaction equation

HRID 2053376 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:18][S:19]([C:22]2[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=2)(=[O:21])=[O:20])=[C:6]([CH:17]=1)[C:7]([NH:9][C:10]1[CH:15]=[CH:14][C:13]([SH:16])=[CH:12][CH:11]=1)=[O:8].[CH3:29][C:30]([O-])(C)[CH3:31].[K+].C(Br)(C)C>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:18][S:19]([C:22]2[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=2)(=[O:21])=[O:20])=[C:6]([CH:17]=1)[C:7]([NH:9][C:10]1[CH:15]=[CH:14][C:13]([S:16][CH:30]([CH3:31])[CH3:29])=[CH:12][CH:11]=1)=[O:8]

Participants

5

Reactant 3

HCID 63582-BromopropaneHCID 22495824HCID 22495824, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 53771469HCID 53771469, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1.00 g (2.21 mmol) of 5-chloro-2-(4-chloro-phenylsulfonylamino)-N-(4-mercapto-phenyl)-benzamide were dissolved in 25 ml of dimethylformamide and 0.25 g (2.21 mmol) of potassium tert-butylate were added. The mixture was stirred at room temperature for 15 min, then 0.27 g (2.21 mmol) of isopropyl bromide were added dropwise, and the mixture was heated to 60° C. for 8 h. For working up it was poured onto water and extracted with ethyl acetate. The combined extracts were evaporated and the residue was purified by chromatography over silica with hexane/ethyl acetate (3:1). 420 mg (39%) of the title compound having a melting point of 168-169° C. were obtained.

Workup

  1. temperaturethe mixture was heated to 60° C. for 8 h
  2. additionwas poured onto water
  3. extractionextracted with ethyl acetate
  4. customThe combined extracts were evaporated
  5. customthe residue was purified by chromatography over silica with hexane/ethyl acetate (3:1)
  6. customwere obtained

Sources & evidence

ORD record
ord-dd214129359a4802bdb91e96039107e8
Source dataset
uspto-grants-2008_02
Patent number
US07326789B2

Reaction notes

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