Dimethylsulphamoyl chloride → 3-(N,N-dimethylamino)sulfonylaminomethylimidazo[5,1-b]thiazole

HRID 1603472Notes

Reaction equation

HRID 1603472 reaction equation
[NH2:1][CH2:2][C:3]1[N:4]2[CH:10]=[N:9][CH:8]=[C:5]2[S:6][CH:7]=1.[CH3:11][N:12]([CH3:17])[S:13](Cl)(=[O:15])=[O:14].C(=O)([O-])O.[Na+]>ClCCl.CN(C)C1C=CN=CC=1>[CH3:11][N:12]([S:13]([NH:1][CH2:2][C:3]1[N:4]2[CH:10]=[N:9][CH:8]=[C:5]2[S:6][CH:7]=1)(=[O:15])=[O:14])[CH3:17]

Participants

6

Reactant 3

HCID 83372Dimethylsulphamoyl chlorideHCID 516892Sodium BicarbonateHCID 196051553-Aminomethylimidazo[5,1-b]thiazole

Product 1

HCID 196051593-(N,N-dimethylamino)sulfonylaminomethylimidazo[5,1-b]thiazole

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A 210 mg potion of 3-aminomethylimidazo[5,1-b]thiazole was dissolved in 4 ml of dichloromethane, and 202 mg of 4-dimethylaminopyridine and 0.179 ml of N,N-dimethylsulfamoyl chloride were further added, followed by stirring for 2.5 hours. Then, to the reaction solution, an aqueous semi-saturated sodium hydrogencarbonate solution were added, and extraction was then carried out three times with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate and then filtered, and the solvent was then evaporated under reduced pressure. Afterward, the resulting residue was purified by a silica gel column chromatograph to obtain 177 mg of the title compound.

Workup

  1. extractionextraction
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. customthe solvent was then evaporated under reduced pressure
  5. customAfterward, the resulting residue was purified by a silica gel column chromatograph

Sources & evidence

ORD record
ord-2bf87ac148364d89b828ac028027a872
Source dataset
uspto-grants-1999_11
Patent number
US05990101

Reaction notes

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