Dimethylformamide → HCID 53923823, compound

HRID 343931Notes

Reaction equation

HRID 343931 reaction equation
C([C:3]1[CH:10]=[CH:9][C:6]([CH:7]=O)=[C:5](F)[CH:4]=1)#N.[C:12]1([SH:18])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[C:19](=[O:22])([O-])[O-].[K+].[K+].[CH3:25][N:26](C)C=O>O>[CH2:7]([S:18][C:12]1[CH:17]=[C:16]([C:25]#[N:26])[CH:15]=[CH:14][C:13]=1[CH:19]=[O:22])[C:6]1[CH:5]=[CH:4][CH:3]=[CH:10][CH:9]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7969ThiophenolHCID 11430Potassium CarbonateHCID 27831503-Fluoro-4-formylbenzonitrile

Product 1

HCID 53923823HCID 53923823, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 4-cyano-2-fluorobenzaldehyde (1.49 g, 10 mmol), phenyl mercaptan (1.39 g, 11 mmol), potassium carbonate (1.51 g, 11 mmol) in dimethylformamide (20 ml) was heated with stirring under a nitrogen atmosphere for 1 hour 40 minutes at 90° C. The yellow solution was cooled, then diluted with water (40-50 ml). The resulting precipitate was filtered and washed with more water, then dried. Recrystallisation from isopropanol gave 2-benzylthio-4-cyanobenzaldehyde as a yellow solid, m.p. 106°-109° C.

Workup

  1. temperaturewas heated
  2. temperatureThe yellow solution was cooled
  3. filtrationThe resulting precipitate was filtered
  4. washwashed with more water
  5. customdried
  6. customRecrystallisation from isopropanol

Sources & evidence

ORD record
ord-d6eeea4f67e8436f88a61e77f5e134d4
Source dataset
uspto-grants-1999_01
Patent number
US05863947

Reaction notes

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