Dimethylformamide → HCID 20033719, compound

HRID 231675Notes

Reaction equation

HRID 231675 reaction equation
[H-].[Na+].CN(C=O)C.[S:8]1[CH:12]=[CH:11][CH:10]=[C:9]1[SH:13].[F:14][C:15]1[CH:16]=[C:17]([CH:20]=[CH:21][C:22]=1F)[C:18]#[N:19]>O>[C:18]([C:17]1[CH:20]=[CH:21][C:22]([S:13][C:9]2[S:8][CH:12]=[CH:11][CH:10]=2)=[C:15]([F:14])[CH:16]=1)#[N:19]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 5226742-ThiophenethiolHCID 5872033,4-Difluorobenzonitrile

Product 1

HCID 20033719HCID 20033719, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Sodium hydride (1.80 g 60% dispersion in oil, 0.045 mol) was washed with petroleum ether then suspended in freshly degassed DMF (50 ml). Thiophene thiol (5.22 g, 0.045 mol) was added dropwise under nitrogen and the mixture was stirred until gas evolution ceased. 3,4-Difluorobenzonitrile (5.0 g, 0.036 mol) was added portionwise and the mixture was refluxed about 1.5 hours, after which the mixture was cooled to room temperature. The reaction mixture was poured into cold H2O and extracted with 3×100 ml ether. The ether extracts were washed with water and brine, then treated with decolorizing carbon and magnesium sulfate. After filtration and evaporation of the solvent the residual (8.46 g) oil crystallized.

Workup

  1. temperaturethe mixture was refluxed about 1.5 hours
  2. extractionextracted with 3×100 ml ether
  3. washThe ether extracts were washed with water and brine
  4. additiontreated with decolorizing carbon and magnesium sulfate
  5. filtrationAfter filtration and evaporation of the solvent the residual (8.46 g) oil
  6. customcrystallized

Sources & evidence

ORD record
ord-a31b6e75c8a9407cbad2f7ff9f78b980
Source dataset
uspto-grants-1989_07
Patent number
US04847289

Reaction notes

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