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

HRID 1983553Notes

Reaction equation

HRID 1983553 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-23a35b4fc4f94214a9b1395a2c153b73
Source dataset
uspto-grants-2009_06
Patent number
US07541464B2

Reaction notes

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