Cyanoacetamide → 1,2-Dihydro-6-(4-fluorophenyl)-5-[4-(methylthio)phenyl]-2-oxo-pyridine-3-carbonitrile

HRID 2293465Notes

Reaction equation

HRID 2293465 reaction equation
[H-].[Na+].CN([C:6]([C:18]1[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=1)=[C:7]([C:10]1[CH:15]=[CH:14][C:13]([S:16][CH3:17])=[CH:12][CH:11]=1)[CH:8]=O)C.[C:25]([CH2:27][C:28]([NH2:30])=[O:29])#[N:26].P([O-])(O)(O)=O.[Na+]>CN(C)C=O.CO>[F:24][C:21]1[CH:22]=[CH:23][C:18]([C:6]2[NH:30][C:28](=[O:29])[C:27]([C:25]#[N:26])=[CH:8][C:7]=2[C:10]2[CH:11]=[CH:12][C:13]([S:16][CH3:17])=[CH:14][CH:15]=2)=[CH:19][CH:20]=1

Participants

7

Reactant 4

HCID 7898CyanoacetamideHCID 24758Sodium hydrideHCID 23672064Monosodium phosphateHCID 541784881-(N,N-dimethylamino)-1-(4-fluorophenyl)-2-(4-methylthiophenyl)prop-1-en-3-one

Product 1

HCID 154085741,2-Dihydro-6-(4-fluorophenyl)-5-[4-(methylthio)phenyl]-2-oxo-pyridine-3-carbonitrileYield 91.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

To 1.45 g of 60% dispersion of sodium hydride in mineral oil (containing 869 mg, 36.2 mMol), washed once with hexane, in 20 ml of dry dimethylformamide, was added dropwise a solution of 9.42 g (29.9 mMol) of 1-(N,N-dimethylamino)-1-(4-fluorophenyl)-2-(4-methylthiophenyl)prop-1-en-3-one from Step 4, cyanoacetamide (2.59 g, 30.3 mMol), and 2.9 ml of methanol in 50 ml of dimethylformamide. After the addition was complete, the resulting dark solution was stirred overnight at 70°-80° C. After cooling, the mixture was added in portions to 500 ml of 1M aqueous sodium dihydrogen phosphate, producing a yellow solid. The solid was filtered, washed with water, and dried to give 9.24 g of 1,2-dihydro-6-(4-fluorophenyl)-5-[4-(methylthio)phenyl]-2-oxo-pyridine-3-carbonitrile.

Workup

  1. washwashed once with hexane, in 20 ml of dry dimethylformamide
  2. additionAfter the addition
  3. temperatureAfter cooling
  4. customproducing a yellow solid
  5. filtrationThe solid was filtered
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-991399cb5106412eb0ea7db0f9ca11cd
Source dataset
uspto-grants-1997_11
Patent number
US05686470

Reaction notes

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