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

HRID 902872

Reaction equation

HRID 902872 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.C(Cl)Cl>[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]thiazole

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

Benzenesulfonamide (638 mg) and 4,5-bis(bromomethyl)thiazole (M. Al. Hariri, O. Galley, F. Pautet, H. Fillion, Eur. J. Org. Chem., 1998, 593-594.) (1.10 g) were dissolved in N,N-dimethylformamide (10 ml), sodium hydride (60% in oil, 357 mg) was added at a time, and the mixture was stirred at room temperature for 3 hours. Water and methylene chloride were added to conduct liquid separation. After the resultant organic layer was dried over anhydrous sodium sulfate, the solvent was distilled off, and the residue was purified by column chromatography on silica gel (methylene chloride:ethyl acetate=9:1) to obtain the title compound (137 mg).

Workup

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

Sources & evidence

ORD record
ord-39e55d46c1b1468caadb96261d27420d
Source dataset
uspto-grants-2008_04
Patent number
US07365205B2

Linked notes

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