Sodium → HCID 20205053, compound

HRID 978074Notes

Reaction equation

HRID 978074 reaction equation
[Na].[CH2:2]([S:9][C:10]1[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][C:11]=1[C:12]([O:14]C)=O)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1>CN(C)C=O>[OH:14][C:12]1[C:11]2[CH:16]=[C:17]([C:20]([F:23])([F:22])[F:21])[CH:18]=[CH:19][C:10]=2[S:9][C:2]=1[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 5360545SodiumHCID 20205041HCID 20205041, compound

Product 1

HCID 20205053HCID 20205053, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
0 °C

Procedure

To a suspension of sodium hyride (50% dispersion in mineral oil) (0.49 g, 10.2 mmol) in N,N-dimethylformamide (30 ml) cooled to 0° C. in an ice-bath was added dropwise with stirring a solution of methyl 2-benzylthio-5-trifluoromethylbenzoate (2.5 g, 7.7 mmol) in N,N-dimethylformamide (10 ml). The reaction mixture was stirred at 75° C. for 1.5 hours under a nitrogen atmosphere, cooled and then poured into ice containing 1N hydrochloric acid. Extraction was effected with diethyl ether. The combined organic extracts were washed three times with water, once with saturated aqueous sodium chloride solution, dried (sodium sulfate) and evaporated. The residue was subjected to chromatography on a column of silica gel (Merck No. 7734) that was eluted with 10:1 hexane-ether. Fractions containing pure product were combined and evaporated to give a white solid that was recrystallized from toluene; yield 490 mg (22%), m/z 1294 (M+.).

Workup

  1. additionwas added dropwise
  2. temperaturecooled
  3. extractionExtraction
  4. washThe combined organic extracts were washed three times with water
  5. dry with materialonce with saturated aqueous sodium chloride solution, dried (sodium sulfate)
  6. customevaporated
  7. wash7734) that was eluted with 10:1 hexane-ether
  8. additionFractions containing pure product
  9. customevaporated
  10. customto give a white solid
  11. customthat was recrystallized from toluene

Sources & evidence

ORD record
ord-cd3a41ea91b84bfa94f5935e0ca247ad
Source dataset
uspto-grants-1987_05
Patent number
US04663344

Reaction notes

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