Chlorosulfamic acid → 3-(Aminosulfonyl)aminomethylimidazo[5,1-b]thiazole
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.C(N(CC)C(C)C)(C)C.[S:20](Cl)(=[O:23])(=[O:22])[NH2:21]>CN(C=O)C>[NH2:21][S:20]([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:23])=[O:22]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -25 °C
Procedure
A 770 mg potin of 3-aminomethylimidazo[5,1-b]thiazole was dissolved in 15 ml of DMF, and 4.78 ml of N,N-diisopropylethylamine and 1.04 g of sulfamoyl chloride were further added at -60° C., followed by stirring at -30 to -20° C. for 4 hours. The reaction solution was concentrated under reduced pressure and then dissolved in 30 ml of water, and the solution was adjusted to pH 7.5 with an aqueous sodium hydrogencarbonate solution. After purification by Diaion HP-20 Resin, crystallization was carried out from methanol to obtain 636 mg of the title compound.
Workup
- concentrationThe reaction solution was concentrated under reduced pressure
- dissolutiondissolved in 30 ml of water
- customAfter purification
- customby Diaion HP-20 Resin, crystallization
Sources & evidence
- ORD record
- ord-5ccbb9ab523f476e8bb9fe9ba7d8887c
- Source dataset
- uspto-grants-1999_11
- Patent number
- US05990101
Reaction notes
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