Hydroxyacetonitrile → HCID 10647295, compound

HRID 1603142Notes

Reaction equation

HRID 1603142 reaction equation
[CH3:1][NH:2][CH:3]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[N:7]([C:14](=[O:31])[C:15]2[CH:20]=[CH:19][C:18]([NH:21][C:22](=[O:30])[C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[CH3:29])=[CH:17][CH:16]=2)[CH2:6][CH2:5][CH2:4]1.[C:32](#[N:35])[CH2:33]O>CO>[CH3:1][N:2]([CH:3]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[N:7]([C:14](=[O:31])[C:15]2[CH:20]=[CH:19][C:18]([NH:21][C:22](=[O:30])[C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[CH3:29])=[CH:17][CH:16]=2)[CH2:6][CH2:5][CH2:4]1)[CH2:33][C:32]#[N:35]

Participants

4

Reactant 2

HCID 7857Hydroxyacetonitrile2×HCID 10716676HCID 10716676, compound

Product 1

HCID 10647295HCID 10647295, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 5-methylamino-1-[4-(2-methylbenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzazepine (0.6 g) in methanol (10 ml) is added glycolonitrile (50%, 0.19 ml) and the mixture is stirred at room temperature for 20 minutes, and then refluxed for 30 minutes. Thereto is added additional glycolonitrile (0.5 ml) and the mixture is refluxed for 5.5 hours. The reaction solution is concentrated and to the resulting residue is added ethyl acetate. The precipitated crystal is collected by filtration, and recrystallized from acetonitrile to give 5-(N-methyl-N-cyanomethylamino)-1-[4-(2-methylbenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzazepine (0.32 g) as colorless needles, m.p. 227-228° C.

Workup

  1. temperaturerefluxed for 30 minutes
  2. temperaturethe mixture is refluxed for 5.5 hours
  3. concentrationThe reaction solution is concentrated and to the resulting residue
  4. additionis added ethyl acetate
  5. filtrationThe precipitated crystal is collected by filtration
  6. customrecrystallized from acetonitrile

Sources & evidence

ORD record
ord-81db645a579c40fa8b204cad629a813b
Source dataset
uspto-grants-1999_11
Patent number
US05985869

Reaction notes

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