Dimethylformamide dimethyl acetal → 8-Chloro-1-(2-chlorophenyl)-4-dimethylaminomethylidene-3,4-dihydro-2-benzazepin-5-one

HRID 1979567Notes

Reaction equation

HRID 1979567 reaction equation
[Cl:1][C:2]1[CH:20]=[CH:19][C:5]2[C:6](=[O:18])[CH2:7][CH2:8][N:9]=[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[Cl:17])[C:4]=2[CH:3]=1.CO[CH:23](OC)[N:24]([CH3:26])[CH3:25]>>[Cl:1][C:2]1[CH:20]=[CH:19][C:5]2[C:6](=[O:18])[C:7](=[CH:23][N:24]([CH3:26])[CH3:25])[CH2:8][N:9]=[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[Cl:17])[C:4]=2[CH:3]=1

Participants

3

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 129482758-chloro-1-(2-chlorophenyl)-3,4-dihydro-5H-2-benzazepin-5-one

Product 1

HCID 536569248-Chloro-1-(2-chlorophenyl)-4-dimethylaminomethylidene-3,4-dihydro-2-benzazepin-5-one

Procedure

A mixture of 18.6 g (61 mmole) of 8-chloro-3,4-dihydro-1-(2-chlorophenyl)-5H-2-benzazepin-5-one and 149 ml of dimethylformamide dimethyl acetal was gently heated (ca 50°) for 12 hr. The mixture was concentrated at reduced pressure to dryness. The residue was crystallized from a mixture of ether and methylene chloride to give the end product as a yellow solid, mp 170°-171° C. Recrystallization from the ether gave yellow prisms, mp 170°-171° C.

Workup

  1. temperaturewas gently heated (ca 50°) for 12 hr
  2. concentrationThe mixture was concentrated at reduced pressure to dryness
  3. customThe residue was crystallized from a mixture of ether and methylene chloride

Sources & evidence

ORD record
ord-4ef97317adf8492ba203534c4676baea
Source dataset
uspto-grants-1984_11
Patent number
US04481142

Reaction notes

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