Water → HCID 10712381, compound

HRID 1779425Notes

Reaction equation

HRID 1779425 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][CH: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])=[CH: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 15814262HCID 15814262, compound

Product 1

HCID 10712381HCID 10712381, compound

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

Thionyl chloride (110 μl, 1.51 mmol) is added to 3,3,3-trifluoro-2-hydroxy-2-methylpropanoic acid (240 mg, 1.52 mmol) in 5 ml of N,N-dimethylacetamide at -15°/-10° C., and the mixture is stirred at this temperature for one hour. Then 2-amino-5-(phenylcarbonyl) thiophene (200 mg, 0.983 mmol) is added and the reaction mixture is equilibrated to room temperature. After the reaction has ended, the reaction mixture is poured into 200 ml of water and subjected to extraction with 3×100 ml of ethyl acetate. The combined organic phases are dried over magnesium sulfate and filtered and the solvent is distilled off. The orange-colored oil which remains is purified by flash chromatography (eluent: 50% v/v ethyl acetate in petroleum ether (40/60)).

Workup

  1. customis equilibrated to room temperature
  2. extractionsubjected to extraction with 3×100 ml of ethyl acetate
  3. dry with materialThe combined organic phases are dried over magnesium sulfate
  4. filtrationfiltered
  5. distillationthe solvent is distilled off
  6. customThe orange-colored oil which remains is purified by flash chromatography (eluent: 50% v/v ethyl acetate in petroleum ether (40/60))

Sources & evidence

ORD record
ord-b0fbcdd9471e4e3aa3c61ffa1e84eb09
Source dataset
uspto-grants-1997_05
Patent number
US05627198

Reaction notes

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