Triethylamine → HCID 23449100, compound

HRID 989844Notes

Reaction equation

HRID 989844 reaction equation
Cl.[CH3:2][NH:3][O:4][CH3:5].C(N(CC)CC)C.Cl[S:14]([C:17]1[N:18]=[CH:19][N:20]2[CH:24]=[CH:23][S:22][C:21]=12)(=[O:16])=[O:15].C(OCC)(=O)C>CN(C=O)C>[CH3:5][O:4][N:3]([CH3:2])[S:14]([C:17]1[N:18]=[CH:19][N:20]2[CH:24]=[CH:23][S:22][C:21]=12)(=[O:15])=[O:16]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 234490387-Chlorosulfonylimidazo[5,1-b]thiazole

Product 1

HCID 23449100HCID 23449100, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N,O-Dimethylhydroxylamine hydrochloride (0.23 g) and 0.56 ml of triethylamine were added to a solution of 0.44 g of 7-chlorosulfonylimidazo[5,1-b]thiazole in 5 ml of DMF. The mixture was stirred at room temperature for one hr. Ethyl acetate was added thereto, followed by washing with water and saturated brine in that order. The organic layer was dried over anhydrous magnesium sulfate. The solvent was removed by distillation. The residue was purified by column chromatography on silica gel (hexane:ethyl acetate=1:2) to give 0.44 g of 7-(N-methoxy-N-methylsulfamoyl)imidazo[5,1-b]thiazole.

Workup

  1. washby washing with water and saturated brine in that order
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. customThe solvent was removed by distillation
  4. customThe residue was purified by column chromatography on silica gel (hexane:ethyl acetate=1:2)

Sources & evidence

ORD record
ord-bfe86584714e4b49a398fd1729576682
Source dataset
uspto-grants-2002_10
Patent number
US06458780B1

Reaction notes

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