Thioacetamide → 6-Methyl-5-(2-methyl-1,3-thiazol-4-yl)-2-oxo-1,2-dihydropyridine-3-carbonitrile

HRID 1982209Notes

Reaction equation

HRID 1982209 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:6]=[C:7]([C:13]#[N:14])[C:8](=[O:12])[NH:9][C:10]=1[CH3:11])=O.[C:15]([NH2:18])(=[S:17])[CH3:16]>CN(C)C=O>[CH3:11][C:10]1[NH:9][C:8](=[O:12])[C:7]([C:13]#[N:14])=[CH:6][C:5]=1[C:3]1[N:18]=[C:15]([CH3:16])[S:17][CH:2]=1

Participants

4

Reactant 2

HCID 2723949ThioacetamideHCID 155921665-Bromoacetyl-1,2-dihydro-6-methyl-2-oxo-3-pyridinecarbonitrile

Product 1

HCID 28012566-Methyl-5-(2-methyl-1,3-thiazol-4-yl)-2-oxo-1,2-dihydropyridine-3-carbonitrileYield 38.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture containing 25.4 g of 5-(bromoacetyl)-1,2-dihydro-6-methyl-2-oxo-3-pyridine-carbonitrile, 7.5 g of thioacetamide and 100 ml of dimethylformamide was heated with stirring on a steam bath for 5 hours and then concentrated on a rotary evaporator. To the residual material was added 100 ml of water and 10 ml of concentrated aqueous ammonium hydroxide. The resulting mixture was filtered and the filtrate reacidified by adding acetic acid. The solid that separated was collected, washed with water and dried, and then recrystallized from dimethylformamide to produce 8.8 g of 1,2-dihydro-6-methyl-5-(2-methyl-4-thiazolyl)-2-oxo-3-pyridinecarbonitrile, m.p. 305°-307° C. with decomposition.

Workup

  1. temperaturewas heated
  2. concentrationconcentrated on a rotary evaporator
  3. additionTo the residual material was added 100 ml of water and 10 ml of concentrated aqueous ammonium hydroxide
  4. filtrationThe resulting mixture was filtered
  5. additionby adding acetic acid
  6. customThe solid that separated
  7. customwas collected
  8. washwashed with water
  9. customdried
  10. customrecrystallized from dimethylformamide

Sources & evidence

ORD record
ord-1d2e811704404930a08ec2a8f1d5cbd5
Source dataset
uspto-grants-1986_06
Patent number
US04595762

Reaction notes

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