4-(Trifluoromethyl)thiobenzamide → HCID 57713028, compound

HRID 2103429Notes

Reaction equation

HRID 2103429 reaction equation
[CH3:1][O:2][C:3](=[O:12])[CH:4](Cl)[C:5](=O)[CH2:6][CH2:7][CH2:8][CH3:9].[F:13][C:14]([F:25])([F:24])[C:15]1[CH:23]=[CH:22][C:18]([C:19]([NH2:21])=[S:20])=[CH:17][CH:16]=1>C(O)C>[CH3:1][O:2][C:3]([C:4]1[S:20][C:19]([C:18]2[CH:17]=[CH:16][C:15]([C:14]([F:24])([F:13])[F:25])=[CH:23][CH:22]=2)=[N:21][C:5]=1[CH2:6][CH2:7][CH2:8][CH3:9])=[O:12]

Participants

4

Reactant 2

HCID 27348234-(Trifluoromethyl)thiobenzamideHCID 57713025Methyl 2-chloro-3-oxoheptanoate

Product 1

HCID 57713028HCID 57713028, compoundYield 69.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 3-oxo-heptanoic acid methyl ester (5.0 g, 31.6 mmol) in dry dichloromethane (80 mL) add sulfurylchloride (2.82 mL). Stir the reaction mixture at room temperature for 30 minutes then add water (20 mL) and the reaction mixture extracted five times with portions of 30 mL of dichloromethane. Wash the combined organic extracts with water, saturated aqueous solution of NaHCO3 and brine and then dry over MgSO4. Remove the solvent under reduced pressure to give 2-chloro-3-oxo-heptanoic acid methyl ester (6.0 g), which was used in the next step without further purification. To a solution of 2-chloro-3-oxo-heptanoic acid methyl ester (6.0 g, 31.1 mmol) in ethanol (50 mL) add 4-(trifluoromethyl) thiobenzamide (6.4 g, 31.2 mmol). Heat the reaction mixture to reflux overnight. Remove the solvent under reduced pressure and purify the residue by chromatography on silica gel (eluting with a gradient of n-heptane:ethyl acetate (100:1 to 60:1)) to give 4-butyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-carboxylic acid methyl ester (7.4 g) as a yellow oil.

Workup

  1. customwas used in the next step without further purification
  2. temperatureHeat the reaction mixture
  3. temperatureto reflux overnight
  4. customRemove the solvent under reduced pressure
  5. custompurify the residue by chromatography on silica gel (
  6. washeluting with a gradient of n-heptane:ethyl acetate (100:1 to 60:1))

Sources & evidence

ORD record
ord-7eee5a3c909140e2ab4b81dfde106d47
Source dataset
uspto-grants-2009_08
Patent number
US07576109B2

Reaction notes

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