Water → HCID 17923438, compound

HRID 396834Notes

Reaction equation

HRID 396834 reaction equation
[F:1][C:2]([F:22])([F:21])[C:3](=[O:20])[CH2:4][C:5]([C:7]1[CH:12]=[CH:11][C:10]([C:13]2[N:14]=[CH:15][S:16][CH:17]=2)=[C:9]([O:18]C)[CH:8]=1)=[O:6].C[S-].[Na+].O>CN(C=O)C>[F:22][C:2]([F:1])([F:21])[C:3](=[O:20])[CH2:4][C:5]([C:7]1[CH:12]=[CH:11][C:10]([C:13]2[N:14]=[CH:15][S:16][CH:17]=2)=[C:9]([OH:18])[CH:8]=1)=[O:6]

Participants

5

Reactant 3

HCID 962WaterHCID 4378561Sodium methanethiolateHCID 22316870HCID 22316870, compound

Product 1

HCID 17923438HCID 17923438, compoundYield 99.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

To a stirred solution of 4,4,4-trifluoro-1-[3-methoxy-4-(1,3-thiazol-4-yl)phenyl]-1,3-butanedione (395 mg, 1.2 mmol) in DMF (6 ml) was added sodium thiomethoxide (420 mg, 6.0 mmol) and the mixture was heated at 120° C. for 3 hours. The mixture was cooled down to room temperature, and poured into water. The whole was extracted with ethyl acetate. The organic layer was washed with brine, dried over MgSO4, and concentrated in vacuo to give title compound (378 mg, 99% yield).

Workup

  1. temperatureThe mixture was cooled down to room temperature
  2. extractionThe whole was extracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d9dfc7cade584031a39d31a7748feec9
Source dataset
uspto-grants-2003_08
Patent number
US06608095B2

Reaction notes

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