Isobutyronitrile → HCID 21395181, compound

HRID 2071606Notes

Reaction equation

HRID 2071606 reaction equation
[NH2-].[Na+].[NH2:3][C:4]1[CH:17]=[CH:16][CH:15]=[CH:14][C:5]=1[C:6]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:7].[C:18](#[N:22])[CH:19]([CH3:21])[CH3:20]>CCOCC>[NH2:22][C:18]1[C:19]([CH3:21])([CH3:20])[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)([OH:7])[C:5]2[C:4](=[CH:17][CH:16]=[CH:15][CH:14]=2)[N:3]=1

Participants

5

Reactant 3

HCID 6559IsobutyronitrileHCID 24533Sodium amideHCID 760802-Aminobenzophenone

Product 1

HCID 21395181HCID 21395181, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Sodium amide (15 g.) was added portionwise to a stirred solution of 2-aminobenzophenone(19.7g., 0.1 mole) and isobutyronitrile (20.7g., 0.3 mole) in dry ether (500 ml.). The mixture was stirred for 1 hour at room temperature and then heated under reflux for 21/2 hours. After cooling, the mixture was poured onto ice, extracted with ether and the combined extracts washed and dried (MgSO4). The solvent was removed and the residue crystallised from toluene to give a product (10.76g., m.p. 157° - 160° C). Recrystallisation from toluene gave the pure title compound, 9.17g., m.p. 161° - 163° C. [Found: C. 76.75, H, 6.9, N, 10.5%. C17H18N2O requires C, 76.65, H, 6.8, N, 10.5%].

Workup

  1. temperatureheated
  2. temperatureunder reflux for 21/2 hours
  3. temperatureAfter cooling
  4. additionthe mixture was poured onto ice
  5. extractionextracted with ether
  6. washthe combined extracts washed
  7. dry with materialdried (MgSO4)
  8. customThe solvent was removed
  9. customthe residue crystallised from toluene
  10. customto give a product (10.76g., m.p. 157° - 160° C)
  11. customRecrystallisation from toluene

Sources & evidence

ORD record
ord-b54477ff4417465cbe7289df3381ea2d
Source dataset
uspto-grants-1977_09
Patent number
US04048177

Reaction notes

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