Dimethyl Sulfoxide → 7,7-Dimethyl-2-phenyl-5-(3-diethylamino-propyl)-5H,7H-imidazo[4,5-h]isoquinoline-4,6-dione dihydrochloride

HRID 47113Notes

Reaction equation

HRID 47113 reaction equation
[H-].[Na+].[ClH:3].[CH3:4][C:5]1([CH3:26])[C:14](=[O:15])[CH:13]2[C:8](=[C:9]3[N:19]=[C:18]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)[N:17]=[C:10]3[C:11](=[O:16])[CH2:12]2)[CH:7]=[N:6]1.CS(C)=O.[CH2:31]([N:33]([CH2:38][CH3:39])[CH2:34][CH2:35][CH2:36]Br)[CH3:32]>O>[ClH:3].[ClH:3].[CH3:4][C:5]1([CH3:26])[C:14](=[O:15])[CH:13]2[C:8](=[C:9]3[N:19]=[C:18]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)[N:17]=[C:10]3[C:11](=[O:16])[CH:12]2[CH2:36][CH2:35][CH2:34][N:33]([CH2:38][CH3:39])[CH2:31][CH3:32])[CH:7]=[N:6]1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 24758Sodium hydrideHCID 4152913-bromo-N,N-diethylpropan-1-amineHCID 706104497,7-Dimethyl-2-phenyl-5H,7H-imidazo[4,5-h]isoquinoline-4,6-dione hydrochloride

Product 1

HCID 706104337,7-Dimethyl-2-phenyl-5-(3-diethylamino-propyl)-5H,7H-imidazo[4,5-h]isoquinoline-4,6-dione dihydrochloride

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2.6 gm of a 55% suspension of sodium hydride in oil were added in portions to a mixture of 5.1 gm of 7,7-dimethyl-2-phenyl-5H,7H-imidazo[4,5-h]isoquinoline-4,6-dione hydrochloride and 50 ml of dimethyl sulfoxide. After stirring the mixture at room temperature for one hour, 4.8 gm of 3-diethylamino propyl bromide hdyrobromide were added, and the mixture was heated at 50° C. for 3 hours. The reaction mixture was admixed with water and extracted several times with chloroform. The chloroform phases were evaporated and the residue was purified on a silicagel column. The dihydrochloride was precipitated from acetone with ethereal hydrochloric acid and recrystallized from methanol/acetone.

Workup

  1. temperaturethe mixture was heated at 50° C. for 3 hours
  2. extractionextracted several times with chloroform
  3. customThe chloroform phases were evaporated
  4. customthe residue was purified on a silicagel column
  5. customThe dihydrochloride was precipitated from acetone with ethereal hydrochloric acid
  6. customrecrystallized from methanol/acetone

Sources & evidence

ORD record
ord-694f1ff6c17349548324165bfe018edb
Source dataset
uspto-grants-1979_11
Patent number
US04176184

Reaction notes

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