Water → HCID 57966444, compound

HRID 420586Notes

Reaction equation

HRID 420586 reaction equation
[Cl:1][C:2]1[CH:28]=[CH:27][C:5]2[N:6]=[C:7]([N:9]3[CH2:13][CH2:12][CH:11]([NH:14][S:15]([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=4[N+:24]([O-:26])=[O:25])(=[O:17])=[O:16])[CH2:10]3)[S:8][C:4]=2[CH:3]=1.[H-].[Na+].[CH3:31][O:32][C:33](=[O:43])[CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[C:37]([CH2:41]Br)[CH:36]=1.O>CN(C)C=O>[CH3:31][O:32][C:33](=[O:43])[CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[C:37]([CH2:41][N:14]([CH:11]2[CH2:12][CH2:13][N:9]([C:7]3[S:8][C:4]4[CH:3]=[C:2]([Cl:1])[CH:28]=[CH:27][C:5]=4[N:6]=3)[CH2:10]2)[S:15]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[N+:24]([O-:26])=[O:25])(=[O:16])=[O:17])[CH:36]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 10014651(3-Bromomethyl-phenyl)-acetic acid methyl esterHCID 57966935HCID 57966935, compound

Product 1

HCID 57966444HCID 57966444, compoundYield 60.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N-[1(6-chlorobenzothiazole-2-yl)pyrrolidine-3-yl]-2-nitrobenzenesulfonamide (500 mg) was dissolved in dimethylformamide (5 mL). Sodium hydride (60%, oil, 50 mg) was added thereto and the mixture was stirred at room temperature for 1 hour. (3-bromomethylphenyl)acetic acid methyl ester (305 mg) was added thereto and the mixture was stirred for 16 hours. To the reaction solution was added water and extracted with ethyl acetate. The organic layer was washed with water and brine, and dried over magnesium sulphate. The solvent was evaporated under reduced pressure and the residue was purified by column chromatograph on silica gel to give the title compound (412 mg). Yield: 60%.

Workup

  1. stirringthe mixture was stirred for 16 hours
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over magnesium sulphate
  5. customThe solvent was evaporated under reduced pressure
  6. customthe residue was purified by column chromatograph on silica gel

Sources & evidence

ORD record
ord-846e199b5d25488f83e06776297ec060
Source dataset
uspto-grants-2012_01
Patent number
US08097610B2

Reaction notes

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