2-(Trifluoromethyl)benzoyl chloride → (2Z)-2-(3-butyl-4-methyl-1,3-thiazol-2(3H)-ylidene)-1-[2-(trifluoromethyl)phenyl]ethanone

HRID 448028Notes

Reaction equation

HRID 448028 reaction equation
[I-].[CH2:2]([N+:6]1[C:10]([CH3:11])=[CH:9][S:8][C:7]=1[CH3:12])[CH2:3][CH2:4][CH3:5].[F:13][C:14]([F:25])([F:24])[C:15]1[CH:23]=[CH:22][CH:21]=[CH:20][C:16]=1[C:17](Cl)=[O:18]>C(Cl)Cl.CN(C1C=CN=CC=1)C.CS(C)=O.CO>[CH2:2]([N:6]1[C:10]([CH3:11])=[CH:9][S:8]/[C:7]/1=[CH:12]\[C:17]([C:16]1[CH:20]=[CH:21][CH:22]=[CH:23][C:15]=1[C:14]([F:13])([F:24])[F:25])=[O:18])[CH2:3][CH2:4][CH3:5]

Participants

6

Reactant 2

HCID 675612-(Trifluoromethyl)benzoyl chlorideHCID 691651093-Butyl-2,4-dimethylthiazol-3-ium iodide

Product 1

HCID 69319646(2Z)-2-(3-butyl-4-methyl-1,3-thiazol-2(3H)-ylidene)-1-[2-(trifluoromethyl)phenyl]ethanone

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent3×HCID 22036561Dimethyl sulfoxide methanolSolvent

Procedure

In a 20 mL vial a solution of 3-butyl-2,4-dimethylthiazol-3-ium iodide (47.92 mg, 0.16 mmol) dissolved in CH2Cl2 (0.5 mL) was added, followed by the addition of DMAP (49.24 mg, 0.40 mmol) dissolved in CH2Cl2 (0.8 mL). Then, to the solution was added 2-(trifluoromethyl)benzoyl chloride (33.4 mg, 0.16 mmol) dissolved in CH2Cl2 (0.5 mL). The vial was capped and shaken overnight at room temperature. The residue was dissolved in 1:1 DMSO/MeOH and purified by reverse phase HPLC using a Waters Sunfire C8 column (30×75 mm) eluting with a gradient of acetonitrile and 0.1% trifluoroacetic acid in water at a flow rate of 50 mL/min. Fractions selected by mass spectrometry to provide the title compound. 1H NMR (500 MHz, DMSO-D6/D2O) δ ppm 0.90 (t, 3 H) 1.27-1.38 (m, 2 H) 1.57-1.67 (m, 2 H) 2.27-2.32 (m, 3 H) 3.90-3.97 (m, 2 H) 5.99-6.02 (m, 1 H) 6.56-6.60 (m, 1 H) 7.53-7.62 (m, 2 H) 7.66-7.77 (m, 2 H); MS (ESI) positive ion 342 (M+H).

Workup

  1. additionwas added
  2. customThe vial was capped
  3. custompurified by reverse phase HPLC
  4. washeluting with a gradient of acetonitrile and 0.1% trifluoroacetic acid in water at a flow rate of 50 mL/min

Sources & evidence

ORD record
ord-2daa0178e2534b639f5854b211ea94e2
Source dataset
uspto-grants-2013_07
Patent number
US08481574B2

Reaction notes

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