5-Fluoro-2-(trifluoromethyl)benzoyl chloride → HCID 69323879, compound

HRID 448033Notes

Reaction equation

HRID 448033 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]1[CH:15]=[CH:16][C:17]([C:23]([F:26])([F:25])[F:24])=[C:18]([CH:22]=1)[C:19](Cl)=[O:20]>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:19]([C:18]1[CH:22]=[C:14]([F:13])[CH:15]=[CH:16][C:17]=1[C:23]([F:26])([F:24])[F:25])=[O:20])[CH2:3][CH2:4][CH3:5]

Participants

6

Reactant 2

HCID 27375605-Fluoro-2-(trifluoromethyl)benzoyl chlorideHCID 691651093-Butyl-2,4-dimethylthiazol-3-ium iodide

Product 1

HCID 69323879HCID 69323879, compound

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 5-fluoro-2-(trifluoromethyl)benzoyl chloride (36.2 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 method analogous to that described in Example 53 to provide the title compound. 1H NMR, MS and LC/MS. 1H NMR (500 MHz, DMSO-d6/D2O) δ ppm 0.90 (t, 3 H) 1.29-1.38 (m, 2H) 1.56-1.69 (m, 2 H) 2.28-2.32 (m, 3 H) 3.91-4.00 (m, 2 H) 6.00-6.05 (m, 1 H) 6.58-6.62 (m, 1 H) 7.37-7.45 (m, 2 H) 7.77-7.86 (m, 1 H); MS (ESI) positive ion 360 (M+H).

Workup

  1. additionwas added
  2. customThe vial was capped
  3. custompurified by reverse phase HPLC

Sources & evidence

ORD record
ord-cf158add023d49bcbc3b85582b60203f
Source dataset
uspto-grants-2013_07
Patent number
US08481574B2

Reaction notes

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