Dimethylformamide dimethyl acetal → 1-(2-Chlorophenyl)-3,4-dihydro-4-[(dimethylamino)methylene]-5H-2-benzazepin-5-one

HRID 2417571Notes

Reaction equation

HRID 2417571 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[C:12](=[O:19])[CH2:11][CH2:10][N:9]=1.CO[CH:22](OC)[N:23]([CH3:25])[CH3:24]>>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[C:12](=[O:19])[C:11](=[CH:22][N:23]([CH3:25])[CH3:24])[CH2:10][N:9]=1

Participants

3

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 129482811-(2-chlorophenyl)-3,4-dihydro-5H-2-benzazepin-5-one

Product 1

HCID 538264411-(2-Chlorophenyl)-3,4-dihydro-4-[(dimethylamino)methylene]-5H-2-benzazepin-5-one

Procedure

A mixture of 3.4 g (12.5 mmole) of 1-(2-chlorophenyl)-3,4-dihydro-5H-2-benzazepin-5-one and 28 ml of dimethylformamide dimethyl acetal was refluxed for 2 hr. The mixture was concentrated at reduced pressure and the resulting solid was triturated with ether to give a tan solid, mp 155°-157° C. Recrystallization from a mixture of methylene chloride and ether gave yellow prisms, mp 158°-159° C.

Workup

  1. temperaturewas refluxed for 2 hr
  2. concentrationThe mixture was concentrated at reduced pressure
  3. customthe resulting solid was triturated with ether
  4. customto give a tan solid, mp 155°-157° C
  5. customRecrystallization
  6. additionfrom a mixture of methylene chloride and ether
  7. customgave yellow prisms, mp 158°-159° C.

Sources & evidence

ORD record
ord-6581bf6467c648caae1faffc37b837be
Source dataset
uspto-grants-1984_09
Patent number
US04469633

Reaction notes

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