Ethyl Acetate → 7-(4-Nitrobenzylsulfamoyl)imidazo[5,1-b]thiazole

HRID 989834Notes

Reaction equation

HRID 989834 reaction equation
[N+:1]([C:4]1[CH:11]=[CH:10][C:7]([CH2:8][NH2:9])=[CH:6][CH:5]=1)([O-:3])=[O:2].C(N(C(C)C)CC)(C)C.Cl[S:22]([C:25]1[N:26]=[CH:27][N:28]2[CH:32]=[CH:31][S:30][C:29]=12)(=[O:24])=[O:23].C(OCC)(=O)C>CN(C=O)C>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([CH2:8][NH:9][S:22]([C:25]2[N:26]=[CH:27][N:28]3[CH:32]=[CH:31][S:30][C:29]=23)(=[O:23])=[O:24])=[CH:10][CH:11]=1)([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 291474-NitrobenzylamineHCID 81531DiisopropylethylamineHCID 23449038HCID 23449038, compound

Product 1

HCID 234493057-(4-Nitrobenzylsulfamoyl)imidazo[5,1-b]thiazoleYield 74.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-Nitrobenzylamine (1.24 g) and 2 ml of diisopropylethylamine were added to a solution of 0.95 g of 7-chlorosulfonylimidazo[5,1-b]thiazole in 20 ml of DMF. The mixture was stirred at room temperature for 12 hr. Ethyl acetate was added to the reaction mixture. The mixture was washed with water and saturated brine in that order. The organic layer was dried over anhydrous magnesium sulfate. The solvent was evaporated, and the resultant powder was collected by filtration to give 1.07 g of 7-(4-nitrobenzylsulfamoyl)imidazo[5,1-b]thiazole.

Workup

  1. washThe mixture was washed with water and saturated brine in that order
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. customThe solvent was evaporated
  4. filtrationthe resultant powder was collected by filtration

Sources & evidence

ORD record
ord-b3b9a4c34b004c4388e24bbbf71fe742
Source dataset
uspto-grants-2002_10
Patent number
US06458780B1

Reaction notes

Loading…