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

HRID 2104399Notes

Reaction equation

HRID 2104399 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+]>CN(C)C=O>[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

5

Reactant 3

HCID 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 1

HCID 6228DimethylformamideSolvent

Procedure

Benzenesulfonamide (638 mg) and 4,5-bis(bromomethyl)thiazole (M. Al. Hariri, O. Galley, F. Pautet, H. Fillion, Eur. J. Org. Chem., pp. 593-594 (1998)) (1.10 g) were dissolved in N,N-dimethylformamide (10 mL) under ice cooling, and sodium hydride (60% in oil, 357 mg) was added thereto at a time, followed by stirring at room temperature for 3 hours. The resultant mixture was partitioned between water and methylene chloride, and the organic layer was dried over sodium sulfate anhydrate. The solvent was distilled away, and the residue was purified by silica gel column chromatography (methylene chloride:ethyl acetate=9:1), to thereby give the title compound (137 mg).

Workup

  1. customThe resultant mixture was partitioned between water and methylene chloride
  2. dry with materialthe organic layer was dried over sodium sulfate anhydrate
  3. distillationThe solvent was distilled away
  4. customthe residue was purified by silica gel column chromatography (methylene chloride:ethyl acetate=9:1)

Sources & evidence

ORD record
ord-3dcb7389a64b479c850c831eb236f6bd
Source dataset
uspto-grants-2009_08
Patent number
US07576135B2

Reaction notes

Loading…