Water → HCID 17923438, compound

HRID 497277Notes

Reaction equation

HRID 497277 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-4a9c772fe5b449cda88997f00249a952
Source dataset
uspto-grants-2005_09
Patent number
US06949536B2

Reaction notes

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