Water → 5-(benzenesulfonyl)-4,6-dihydro-5H-pyrrolo[3,4-d]thiazole

HRID 546432

Reaction equation

HRID 546432 reaction equation
[C:1]1([S:7]([NH2:10])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[CH2:12][C:13]1[N:14]=[CH:15][S:16][C:17]=1[CH2:18]Br.[H-].[Na+].O>CN(C)C=O.ClCCl>[C:1]1([S:7]([N:10]2[CH2:18][C:17]3[S:16][CH:15]=[N:14][C:13]=3[CH2:12]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 4

HCID 962WaterHCID 7370BenzenesulfonamideHCID 24758Sodium hydrideHCID 108496984,5-Bis(bromomethyl)thiazole

Product 1

HCID 184428065-(benzenesulfonyl)-4,6-dihydro-5H-pyrrolo[3,4-d]thiazoleYield 12.7%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

Benzenesulfonamide (638 mg) and 4,5-bis(bromo-methyl)thiazole (1.10 g) were dissolved in dimethylformamide (10 ml), 60% sodium hydride in oil (357 mg) was added at a time, and the mixture was stirred at room temperature for 3 hours. Water and dichloromethane were added to conduct liquid separation. After the resultant oil layer was dried over anhydrous sodium sulfate, the solvent was distilled off, and the residue was purified by column chromatography on silica gel (dichloromethane:ethylacetate=9:1) to obtain the title compound (137 mg) as colorless powder.

Workup

  1. customliquid separation
  2. dry with materialAfter the resultant oil layer was dried over anhydrous sodium sulfate
  3. distillationthe solvent was distilled off
  4. customthe residue was purified by column chromatography on silica gel (dichloromethane:ethylacetate=9:1)

Sources & evidence

ORD record
ord-dabc27cbc47a4c8ba6825ec6c4a279b0
Source dataset
uspto-grants-2011_05
Patent number
US07935824B2

Linked notes

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