5-(Bromomethyl)-2-(trifluoromethyl)thiazole → 2-(Trifluoromethyl)-1,3-thiazole

HRID 1927191

Reaction equation

HRID 1927191 reaction equation
BrC[C:3]1[S:7][C:6]([C:8]([F:11])([F:10])[F:9])=[N:5][CH:4]=1>C(O)C>[F:9][C:8]([F:11])([F:10])[C:6]1[S:7][CH:3]=[CH:4][N:5]=1

Participants

3

Reactant 1

HCID 152392195-(Bromomethyl)-2-(trifluoromethyl)thiazole

Product 1

HCID 212818242-(Trifluoromethyl)-1,3-thiazoleYield 96%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 5-(bromomethyl)-2-(trifluoromethyl)-1,3-thiazole [prepared in accordance with U.S. Pat. No. 5,338,856] (170 mg, 069 mmol) in 5 mL of ethanol was treated sodium methylthiolate (60 mg, 0.86 mmol) at room temperature. The reaction was complete in 10 min and so the solvent was carefully removed under reduced pressure (40 mmHg) without heating. The residue was partitioned between dichloromethane and dilute hydrochloric acid, washed with saturated brine and dried over sodium sulfate. The solvent was again carefully removed under reduced pressure (40 mmHg) without heating to yield 5-[methylthio)methyl]-2-(trifluoromethyl)-1,3-thiazole (140 mg; 96%) as a pale orange liquid: 1H NMR (CDCl3) δ 7.75 (s, 1H), 3.90 (s, 2H), 2.10 (s, 3H); GCMS (FID) m/z 213 (M+).

Workup

  1. customso the solvent was carefully removed under reduced pressure (40 mmHg)
  2. temperaturewithout heating
  3. customThe residue was partitioned between dichloromethane and dilute hydrochloric acid
  4. washwashed with saturated brine
  5. dry with materialdried over sodium sulfate
  6. customThe solvent was again carefully removed under reduced pressure (40 mmHg)
  7. temperaturewithout heating

Sources & evidence

ORD record
ord-9d3b74ca2f6d484a99d2d7f24e956437
Source dataset
uspto-grants-2012_05
Patent number
US08183270B2

Linked notes

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