Triethylamine → 4-Butyl-5-chloromethyl-2-(4-trifluoromethyl-phenyl)-thiazole

HRID 2233547Notes

Reaction equation

HRID 2233547 reaction equation
[CH2:1]([C:5]1[N:6]=[C:7]([C:12]2[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][CH:13]=2)[S:8][C:9]=1[CH2:10]O)[CH2:2][CH2:3][CH3:4].C(N(CC)CC)C.CS([Cl:33])(=O)=O>ClCCl>[CH2:1]([C:5]1[N:6]=[C:7]([C:12]2[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][CH:13]=2)[S:8][C:9]=1[CH2:10][Cl:33])[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 58934102HCID 58934102, compound

Product 1

HCID 230893954-Butyl-5-chloromethyl-2-(4-trifluoromethyl-phenyl)-thiazole

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

1.0 g [4-Butyl-2-(4-trifluoromethyl-phenyl)-thiazole-5-yl]-methanol were dissolved in 50 ml dichloromethane, 0.88 ml triethylamine and 0.39 ml methanesulfonyl chloride were added. The reaction mixture was stirred at room temperature for a period of three hours then 100 ml of dichloromethane were added and the reaction mixture washed with 50 ml of saturated NaHCO3 solution, water and brine. The organic layer was dried over MgSO4 and the solvent removed under reduced pressure. This provided 1.0 g 4-Butyl-5-chloromethyl-2-(4-trifluoromethyl-phenyl)-thiazole as yellow oil.

Workup

  1. washthe reaction mixture washed with 50 ml of saturated NaHCO3 solution, water and brine
  2. dry with materialThe organic layer was dried over MgSO4
  3. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-f42c63d3ae3e4082a3c30db624e2da60
Source dataset
uspto-grants-2010_05
Patent number
US07709509B2

Reaction notes

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