Isopropanol → HCID 22258959, compound

HRID 1611212Notes

Reaction equation

HRID 1611212 reaction equation
[C:1]([CH2:3][C:4]([NH2:6])=[O:5])#[N:2].[H-].[Na+].C([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[C:22](=O)[CH:23]=[C:24]([S:27][CH3:28])SC)C1C=CC=CC=1.C[CH:31]([OH:33])[CH3:32]>Cl>[CH2:31]([O:33][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[C:22]1[NH:6][C:4](=[O:5])[C:3](=[C:24]([S:27][CH3:28])[CH:23]=1)[C:1]#[N:2])[C:32]1[CH:20]=[CH:21][CH:16]=[CH:17][CH:18]=1

Participants

6

Reactant 4

HCID 3776IsopropanolHCID 7898CyanoacetamideHCID 24758Sodium hydrideHCID 22258850HCID 22258850, compound

Product 1

HCID 22258959HCID 22258959, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

To a suspension of cyanoacetamide (1.27 g, 15.1 mmol) in 2-propanol (50 mL) was added sodium hydride (60% suspension, 0.605 g, 15.1 mmol). The mixture was stirred at room temperature for 10 min. To this mixture, 1-[2-(benzyl)phenyl]-3,3-bis(methylthio)-2-propene-1-one (5.00 g, 15.1 mmol) was added in one portion. The resulting mixture was refluxed for 4 hrs. After being cooled to room temperature, the mixture was diluted with 1N HCl. The resulting precipitates were collected by filtration and washed with EtOH to give 6-[2-(benzyloxy)phenyl]-4-(methylthio)-2-oxo-1,2-dihydro-nicotinonitrile as a yellow crystalline solid (4.43 g, yield; 84%).

Workup

  1. temperatureThe resulting mixture was refluxed for 4 hrs
  2. temperatureAfter being cooled to room temperature
  3. customThe resulting precipitates
  4. filtrationwere collected by filtration
  5. washwashed with EtOH

Sources & evidence

ORD record
ord-d1ac995749594c0a94a03c58e06406aa
Source dataset
uspto-grants-2006_01
Patent number
US06984649B1

Reaction notes

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