Ethanol → Sodium 3-cyano-6-oxo-1-phenyl-1,6-dihydropyridine-2-thiolate

HRID 735221Notes

Reaction equation

HRID 735221 reaction equation
C[O-].[Na+:3].CCO.CN1[CH:15]=[CH:14][C:12](=[O:13])N(C)C1=O.[C:17]([CH2:19][C:20]([NH:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[S:21])#[N:18]>CO>[C:17]([C:19]1[CH:15]=[CH:14][C:12](=[O:13])[N:22]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:20]=1[S-:21])#[N:18].[Na+:3]

Participants

6

Reactant 4

HCID 702EthanolHCID 701221,3-DimethyluracilHCID 27713122-cyano-N-phenylethanethioamideHCID 10942334Sodium Methoxide

Product 1

HCID 11615758Sodium 3-cyano-6-oxo-1-phenyl-1,6-dihydropyridine-2-thiolate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of sodium methoxide in MeOH (30 wt %, 202.2 g) was added to absolute EtOH (360 ml), followed by 1,3-dimethyluracil (75 g) and 2-cyano-N-phenylthioacetamide (Adhikari et al., Australian J. Chem., 1999, 52, 63-67) (90 g). The resulting mixture was heated at reflux for 8 h and then allowed to cool to ambient temperature overnight. The reaction mixture was then cooled to +5° C. and maintained at this temperature for at least an hour when the product was recovered by filtration. The filter cake was washed with cold (+5° C.) absolute ethanol (450 ml) and then dried to constant weight under vacuum at 45° C. to give the title compound as a pale pink solid (130.0 g). The product thus obtained contained residual EtOH and MeOH, estimated at 12.2 wt % by 1H nmr, corresponding to a corrected yield of 114.1 g. δH (DMSO-d6) 7.32 (2H, m), 7.27-7.18 (1H, m), 7.16 (1H, d, J 9.1 Hz), 6.92 (2H, m), 5.63 (1H, d, J 9.1 Hz). LCMS (Conditions B) (ES+) RT 2.43 minutes, 229 (M+H)+.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureat reflux for 8 h
  3. temperatureThe reaction mixture was then cooled to +5° C.
  4. temperaturemaintained at this temperature for at least an hour when the product
  5. filtrationwas recovered by filtration
  6. washThe filter cake was washed with cold (+5° C.) absolute ethanol (450 ml)
  7. customdried to constant weight under vacuum at 45° C.

Sources & evidence

ORD record
ord-eaf7c0bdd8e6400789f84a9fbc1d604c
Source dataset
uspto-grants-2009_09
Patent number
US07592455B2

Reaction notes

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