Thionyl Chloride → 5-(Chloromethyl)-4-methyl-2-[3-(trifluoromethyl)phenyl]-1,3-thiazole

HRID 1767927Notes

Reaction equation

HRID 1767927 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([F:18])([F:17])[F:16])[CH:10]=2)[S:5][C:6]=1[CH2:7]O.S(Cl)([Cl:21])=O.C(=O)(O)[O-].[Na+]>C(Cl)(Cl)Cl>[Cl:21][CH2:7][C:6]1[S:5][C:4]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([F:18])([F:17])[F:16])[CH:10]=2)=[N:3][C:2]=1[CH3:1]

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 516892Sodium BicarbonateHCID 22647518{4-Methyl-2-[3-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl}methanol

Product 1

HCID 236145055-(Chloromethyl)-4-methyl-2-[3-(trifluoromethyl)phenyl]-1,3-thiazoleYield 94%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of [4-methyl-2-(3-trifluoromethyl-phenyl)-thiazol-5-yl]-methanol (1.2 g, 4.4 mmol) in chloroform (7 ml) was added thionyl chloride (0.64 ml, 8.8 mmol) at −10° C. under an argon atmosphere. The reaction mixture was stirred for 30 min, saturated aqueous sodium bicarbonate solution/ice water 1/1 was added and the layers were separated. The aqueous layer was extracted two times with dichloromethane. The combined organic layers were washed with ice water/brine 1/1 and dried over sodium sulfate. The solvent was evaporated in vacuo to give the title compound (1.2 g, 4.1 mmol, 94%) as yellow oil which was used in the next step without further purification.

Workup

  1. customthe layers were separated
  2. extractionThe aqueous layer was extracted two times with dichloromethane
  3. washThe combined organic layers were washed with ice water/brine 1/1
  4. dry with materialdried over sodium sulfate
  5. customThe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-11107a143e3c47f78b44c83d7bf19a2b
Source dataset
uspto-grants-2007_06
Patent number
US07235572B2

Reaction notes

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