Water → HCID 19956156, compound

HRID 1779429Notes

Reaction equation

HRID 1779429 reaction equation
S(Cl)(Cl)=O.[F:5][C:6]([F:14])([F:13])[C:7]([OH:12])([CH3:11])[C:8](O)=[O:9].[NH2:15][C:16]1[S:17][C:18]([C:21]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[O:22])=[CH:19][N:20]=1.O>CN(C)C(=O)C>[C:23]1([C:21]([C:18]2[S:17][C:16]([NH:15][C:8](=[O:9])[C:7]([OH:12])([CH3:11])[C:6]([F:14])([F:13])[F:5])=[N:20][CH:19]=2)=[O:22])[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24386Thionyl ChlorideHCID 27751253,3,3-Trifluoro-2-hydroxy-2-methylpropanoic acidHCID 19956162HCID 19956162, compound

Product 1

HCID 19956156HCID 19956156, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

Thionyl chloride (80 μl, 1.1 mmol) is added to 3,3,3-trifluoro-2-hydroxy-2-methylpropanoic acid (150 mg, 0.949 mmol) in 5 ml of N,N-dimethylacetamide at -15°/-10° C. and the mixture is stirred at this temperature for one hour. After addition of 2-amino-5-(phenylcarbonyl)thiazole (130 mg, 0.636 mmol) and equilibration to room temperature, the reaction mixture is stirred for 2.5 hours, then poured into 100 ml of water and subjected to extraction with 3×100 ml of ethyl acetate. The combined organic phases are washed with 50 ml of saturated sodium chloride solution, dried over magnesium sulfate and filtered, and the solvent is distilled off. The oil which remains is purified by flash chromatography (eluent: 33% v/v ethyl acetate in petroleum ether (40/60)) to give N-[5-(phenylcarbonyl)thiazol-2-yl]-3,3,3-trifluoro-2-hydroxy-2-methylpropanamide (0.10 g, 46%) as pale yellow crystals. These crystals are digested in dichloromethane.

Workup

  1. stirringthe reaction mixture is stirred for 2.5 hours
  2. extractionsubjected to extraction with 3×100 ml of ethyl acetate
  3. washThe combined organic phases are washed with 50 ml of saturated sodium chloride solution
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. distillationthe solvent is distilled off
  7. customThe oil which remains is purified by flash chromatography (eluent: 33% v/v ethyl acetate in petroleum ether (40/60))

Sources & evidence

ORD record
ord-002925fd42604dffa658b81e782345de
Source dataset
uspto-grants-1997_05
Patent number
US05627198

Reaction notes

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