Potassium Carbonate → 4-Cyano-2-(2-phenylethylthio)benzaldehyde

HRID 343928Notes

Reaction equation

HRID 343928 reaction equation
[C:1]1([CH2:7][CH2:8][SH:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:10]([C:12]1[CH:19]=[CH:18][C:15]([CH:16]=[O:17])=[C:14](F)[CH:13]=1)#[N:11].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.O>[C:10]([C:12]1[CH:19]=[CH:18][C:15]([CH:16]=[O:17])=[C:14]([S:9][CH2:8][CH2:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH:13]=1)#[N:11]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 781262-PhenylethanethiolHCID 27831503-Fluoro-4-formylbenzonitrile

Product 1

HCID 541260724-Cyano-2-(2-phenylethylthio)benzaldehyde

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
75 °C

Procedure

Phenylethylmercaptan (2.14 ml, 16 mmol) was added to a stirred suspension of 4-cyano-2-fluorobenzaldehyde (2.23 g, 15 mmol) and potassium carbonate (2.21 g, 16 mmol) in dimethylformamide (10 ml) at room temperature under nitrogen atmosphere. The mixture was heated to 75° C. for 1 hour, then cooled and diluted with water (15 ml). A yellow solid precipitated and was filtered, washed with water and then crystallised from cyclohexane (250 ml) to give pale needles of 4-cyano-2-(2-phenylethylthio)benzaldehyde, m.p. 89° C.

Workup

  1. temperaturecooled
  2. customA yellow solid precipitated
  3. filtrationwas filtered
  4. washwashed with water
  5. customcrystallised from cyclohexane (250 ml)

Sources & evidence

ORD record
ord-6f8bf4bcdb49401683923101be0ab9ab
Source dataset
uspto-grants-1999_01
Patent number
US05863947

Reaction notes

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