Triethylamine → HCID 59594814, compound

HRID 2263384Notes

Reaction equation

HRID 2263384 reaction equation
[F:1][CH:2]([F:18])[C:3]1[N:4]=[C:5]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=2)[S:6][C:7]=1[CH2:8]O.C(N(CC)CC)C.CS([Cl:30])(=O)=O>ClCCl>[Cl:30][CH2:8][C:7]1[S:6][C:5]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=2)=[N:4][C:3]=1[CH:2]([F:18])[F:1]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 59594668HCID 59594668, compound

Product 1

HCID 59594814HCID 59594814, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2.70 g [4-Difluoromethyl-2-(4-methoxy-phenyl)-thiazol-5-yl]-methanol were dissolved in 15 ml dichloromethane and cooled in an ice bath. 2.07 ml triethylamine were added, followed by the addition of 0.92 ml methanesulfonylchloride. The ice bath was removed and the resulting mixture stirred at room temperature over night. Then 2.07 ml triethylamine and 0.92 ml methanesulfonylchloride were added again and the reaction mixture stirred at room temperature for additional four hours. The reaction mixture was then washed with water and brine, dried over MgSO4 and the solvent removed in vacuo to obtain 3.0 g crude 5-chloromethyl-4-difluoromethyl-2-(4-methoxy-phenyl)-thiazole as an oil which was used without further purification.

Workup

  1. temperaturecooled in an ice bath
  2. customThe ice bath was removed
  3. additionThen 2.07 ml triethylamine and 0.92 ml methanesulfonylchloride were added again
  4. stirringthe reaction mixture stirred at room temperature for additional four hours
  5. washThe reaction mixture was then washed with water and brine
  6. dry with materialdried over MgSO4
  7. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-6f9155f436574d44969293df787d7821
Source dataset
uspto-grants-2010_12
Patent number
US07851493B2

Reaction notes

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