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

HRID 2103431Notes

Reaction equation

HRID 2103431 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

To a solution of [4-butyl-2-(4-trifluoromethyl-phenyl)-thiazole-5-yl]-methanol (1.0 g, 3.1 mmol) in dichloromethane (50 mL) add triethylamine (0.88 mL) and methanesulfonyl chloride (0.39 mL). Stir the reaction mixture at room temperature for a period of three hours then add dichloromethane (100 mL). Wash the reaction mixture with a saturated aqueous solution of NaHCO3 (50 mL), water and brine. Dry the organic layer over MgSO4 and remove the solvent under reduced pressure to give 4-butyl-5-chloromethyl-2-(4-trifluoromethyl-phenyl)-thiazole (1.0 g) as a yellow oil.

Workup

  1. washWash the reaction mixture with a saturated aqueous solution of NaHCO3 (50 mL), water and brine
  2. dry with materialDry the organic layer over MgSO4
  3. customremove the solvent under reduced pressure

Sources & evidence

ORD record
ord-4e4c51a929034430977e430f1a566ee1
Source dataset
uspto-grants-2009_08
Patent number
US07576109B2

Reaction notes

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