Dichloromethane → HCID 17842483, compound

HRID 546437Notes

Reaction equation

HRID 546437 reaction equation
Cl.[CH3:2][C:3]1([NH2:6])[CH2:5][CH2:4]1.ClCCl.CS(O[CH2:15][CH2:16][C:17]1[N:18]=[CH:19][S:20][C:21]=1[CH2:22]OS(C)(=O)=O)(=O)=O>O>[CH3:2][C:3]1([N:6]2[CH2:15][CH2:16][C:17]3[N:18]=[CH:19][S:20][C:21]=3[CH2:22]2)[CH2:5][CH2:4]1

Participants

5

Reactant 3

HCID 6344Dichloromethane2×HCID 12953687(1-Methylcyclopropyl)amine hydrochloride2×HCID 17842439HCID 17842439, compound

Product 1

HCID 17842483HCID 17842483, compoundYield 34.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1-Methylcyclopropylamine hydrochloride (J. Org. Chem., 1989, Vol. 54, p. 1815) (1.89 g) was added to dichloromethane (20 ml) containing 4-(2-methane-sulfonyloxyethyl)-5-methanesulfonyloxymethylthiazole (4.46 g) under ice cooling, and the mixture was stirred overnight at room temperature. 1-Methylcyclopropylamine hydrochloride (1.89 g) was additionally added, and the mixture was stirred for 20 hours at room temperature and 5 hours under refluxing. Dichloromethane and water were added to the reaction mixture to separate an organic layer. The organic layer was dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by column chromatography on silica gel (methanol:dichloromethane=1:49) to obtain the title compound (944 mg) as a pale yellow oil.

Workup

  1. stirringthe mixture was stirred for 20 hours at room temperature and 5 hours
  2. temperatureunder refluxing
  3. customto separate an organic layer
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. customthe residue was purified by column chromatography on silica gel (methanol:dichloromethane=1:49)

Sources & evidence

ORD record
ord-e5b9c0d083f44fa0919ec016e4371bbe
Source dataset
uspto-grants-2011_05
Patent number
US07935824B2

Reaction notes

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