Chlorosulfamic acid → HCID 19605100, compound

HRID 1603475Notes

Reaction equation

HRID 1603475 reaction equation
[CH3:1][NH:2][CH2:3][C:4]1[N:5]2[CH:11]=[N:10][CH:9]=[C:6]2[S:7][CH:8]=1.C(N(CC)C(C)C)(C)C.[S:21](Cl)(=[O:24])(=[O:23])[NH2:22]>CN(C=O)C>[NH2:22][S:21]([N:2]([CH2:3][C:4]1[N:5]2[CH:11]=[N:10][CH:9]=[C:6]2[S:7][CH:8]=1)[CH3:1])(=[O:24])=[O:23]

Participants

5

Reactant 3

HCID 24499Chlorosulfamic acidHCID 81531DiisopropylethylamineHCID 19605154HCID 19605154, compound

Product 1

HCID 19605100HCID 19605100, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A 47 mg potion of 3-(N-methylamino)methylimidazo[5,1-b]thiazole was dissolved in 1 ml of DMF, and 0.305 ml of N,N-diisopropylethylamine and 100 mg of sulfamoyl chloride were further added at -45° C., followed by stirring for 8 hours, while the solution was heated up to room temperature. Then, the reaction solution was concentrated under reduced pressure, and 10 ml of water and an aqueous sodium hydrogencarbonate solution were then added to adjust the solution to pH 9.0. Afterward, extraction was carried out four times with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate and then filtered, and the solvent was evaporated under reduced pressure. The resulting residue was purified by a silica gel column chromatograph to obtain 37.4 mg of the title compound.

Workup

  1. concentrationThen, the reaction solution was concentrated under reduced pressure, and 10 ml of water
  2. additionan aqueous sodium hydrogencarbonate solution were then added
  3. extractionAfterward, extraction
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customthe solvent was evaporated under reduced pressure
  7. customThe resulting residue was purified by a silica gel column chromatograph

Sources & evidence

ORD record
ord-d22a237e63cc449ebdada49948b9860e
Source dataset
uspto-grants-1999_11
Patent number
US05990101

Reaction notes

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