Dimethylcarbamoyl Chloride → N,N-Dimethyl-N'-(4,4-dimethyl-1,2,3,4-tetrahydro-1,3-dioxo-7-isoquinolinyl)-urea

HRID 621419Notes

Reaction equation

HRID 621419 reaction equation
[NH2:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([CH3:15])([CH3:14])[C:7](=[O:13])[NH:8][C:9]2=[O:12])=[CH:4][CH:3]=1.[CH3:16][N:17]([CH3:21])[C:18](Cl)=[O:19]>N1C=CC=CC=1>[CH3:16][N:17]([CH3:21])[C:18]([NH:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([CH3:15])([CH3:14])[C:7](=[O:13])[NH:8][C:9]2=[O:12])=[CH:4][CH:3]=1)=[O:19]

Participants

4

Reactant 2

HCID 6598Dimethylcarbamoyl ChlorideHCID 135581517-amino-4,4-dimethylisoquinoline-1,3(2H,4H)-dione

Product 1

HCID 21242848N,N-Dimethyl-N'-(4,4-dimethyl-1,2,3,4-tetrahydro-1,3-dioxo-7-isoquinolinyl)-urea

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

1.3 g. (6.3 mMole) 7-amino-4,4-dimethylisoquinoline-1,3-dione was dissolved in 30 ml. pyridine, mixed, while cooling with ice, with 1.5 g. dimethylcarbamoyl chloride and the reaction mixture further stirred for 4 hours at 25° C. Subsequently, the reaction mixture was distilled to dryness, the residue was taken up in methylene chloride, washed with water, dried and the methylene chloride distilled off. The residue was recrystallised from ethanol. Yield 1.1 g. (63.6% of theory); m.p. 256°-258° C.

Workup

  1. temperaturewhile cooling with ice, with 1.5 g
  2. distillationSubsequently, the reaction mixture was distilled to dryness
  3. washwashed with water
  4. customdried
  5. distillationthe methylene chloride distilled off
  6. customThe residue was recrystallised from ethanol

Sources & evidence

ORD record
ord-d46dd2ee7094491f8ac07da2da6b03eb
Source dataset
uspto-grants-1989_04
Patent number
US04824835

Reaction notes

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