Hydroxyacetonitrile → HCID 10647295, compound

HRID 745100Notes

Reaction equation

HRID 745100 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-c51751d4f870464dad6ce3b85bba856e
Source dataset
uspto-grants-1996_09
Patent number
US05559230

Reaction notes

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