Water → HCID 9951743, compound

HRID 1779430Notes

Reaction equation

HRID 1779430 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]([S:21]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)(=[O:23])=[O:22])=[CH:19][CH:20]=1.O>CN(C)C(=O)C>[C:24]1([S: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:23])=[O:22])[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24386Thionyl ChlorideHCID 27751253,3,3-Trifluoro-2-hydroxy-2-methylpropanoic acidHCID 19956158HCID 19956158, compound

Product 1

HCID 9951743HCID 9951743, compound

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 (170 mg, 1.08 mmol) in 5 ml of N,N-dimethylacetamide at -15°/-10° C. and the mixture is stirred at this temperature for one hour. After adding 2-amino-5-(phenylsulfonyl)thiophene (170 mg, 0.710 mmol) and equilibration to room temperature and 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. extractionsubjected to extraction with 3×100 ml of ethyl acetate
  2. dry with materialThe combined organic phases are dried over magnesium sulfate
  3. filtrationfiltered
  4. distillationthe solvent is distilled off
  5. 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-753c202fbc094e6aad64ce763f1282d0
Source dataset
uspto-grants-1997_05
Patent number
US05627198

Reaction notes

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