Triethylamine → 5-Chloromethyl-4-methyl-2-(4-trifluoromethyl-phenyl)-thiazole

HRID 2233569Notes

Reaction equation

HRID 2233569 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([C:9]2[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:11][CH:10]=2)[S:5][C:6]=1[CH2:7]O.C(N(CC)CC)C.CS([Cl:30])(=O)=O>ClCCl>[Cl:30][CH2:7][C:6]1[S:5][C:4]([C:9]2[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:11][CH:10]=2)=[N:3][C:2]=1[CH3:1]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 2783005(4-Methyl-2-(4-(trifluoromethyl)phenyl)-1,3-thiazol-5-yl)methanol

Product 1

HCID 27830065-Chloromethyl-4-methyl-2-(4-trifluoromethyl-phenyl)-thiazole

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

3.0 g of [4-Methyl-2-(4-trifluoromethyl-phenyl)-thiazole-5-yl]-methanol were dissolved in 50 ml dichloromethane, 3.0 ml of triethylamine were added followed by the addition of 1.36 ml of methanesulfonylchloride. The reaction mixture was stirred at room temperature for two hours. 100 ml dichloromethane were added and the mixture washed with saturated sodium hydrogen carbonate solution, water and brine. The organic layer was dried over MgSO4. The solvent was removed in vacuo to obtain 3.3 g of crude 5-Chloromethyl-4-methyl-2-(4-trifluoromethyl-phenyl)-thiazole as a brown oil.

Workup

  1. washthe mixture washed with saturated sodium hydrogen carbonate solution, water and brine
  2. dry with materialThe organic layer was dried over MgSO4
  3. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-7cb283cbbdb64a96982a2b182f6d9fd8
Source dataset
uspto-grants-2010_05
Patent number
US07709509B2

Reaction notes

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