Hydrochloric Acid → 3-[(N-allyloxycarbonylamino)sulfonyl]aminomethylimidazo[5,1-b]thiazole

HRID 1603470Notes

Reaction equation

HRID 1603470 reaction equation
[CH2:1]([OH:4])[CH:2]=[CH2:3].Cl[S:6]([N:9]=[C:10]=[O:11])(=[O:8])=[O:7].[NH2:12][CH2:13][C:14]1[N:15]2[CH:21]=[N:20][CH:19]=[C:16]2[S:17][CH:18]=1.C(=O)([O-])[O-].[K+].[K+].Cl>O.C(N(CC)CC)C.ClCCl>[CH2:1]([O:4][C:10]([NH:9][S:6]([NH:12][CH2:13][C:14]1[N:15]2[CH:21]=[N:20][CH:19]=[C:16]2[S:17][CH:18]=1)(=[O:8])=[O:7])=[O:11])[CH:2]=[CH2:3]

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 7858Allyl AlcoholHCID 11430Potassium CarbonateHCID 70918Chlorosulfonyl isocyanateHCID 196051553-Aminomethylimidazo[5,1-b]thiazole

Product 1

HCID 196050753-[(N-allyloxycarbonylamino)sulfonyl]aminomethylimidazo[5,1-b]thiazole

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×HCID 8471TriethylamineSolvent

Procedure

Under an argon atmosphere, 0.68 ml of allyl alcohol was added dropwise to a dry dichloromethane solution containing 0.87 ml of chlorosulfonyl isocyanate at -43° C. with stirring, and the mixture was then stirred at -43 to -37° C. for 30 minutes. This mixed solution was added dropwise to 50 ml of a dry dichloromethane solution containing 766 mg of 3-aminomethylimidazo[5,1-b]thiazole and 1.40 ml of triethylamine at -60° C. under an argon atmosphere, followed by stirring at the same temperature for 1.5 hours. After the addition of distilled water, the solution was adjusted to pH 6.0 with a 15% aqueous potassium carbonate solution and 2N hydrochloric acid, and after salting-out, extraction was carried out five times with ethyl acetate. After the organic layer was dried over anhydrous magnesium sulfate, the solvent was evaporated under reduced pressure. The resulting residue was separated by a silica gel column chromatograph, and then recrystallized from ethanol-diethyl ether to obtain 1135 mg of 3-[(N-allyloxycarbonylamino)sulfonyl]aminomethylimidazo[5,1-b]thiazole as a milky white powder.

Workup

  1. stirringthe mixture was then stirred at -43 to -37° C. for 30 minutes
  2. stirringby stirring at the same temperature for 1.5 hours
  3. extractionextraction
  4. dry with materialAfter the organic layer was dried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe resulting residue was separated by a silica gel column chromatograph
  7. customrecrystallized from ethanol-diethyl ether

Sources & evidence

ORD record
ord-2d5f4ad1d4c74112893ceee05dd98efe
Source dataset
uspto-grants-1999_11
Patent number
US05990101

Reaction notes

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