Chloroform → 2-(4-Dimethylamino-butyl)-5,6-dimethoxy-1-methyl-1H-quinazoline-4-one

HRID 557150Notes

Reaction equation

HRID 557150 reaction equation
[CH3:1][N:2]([CH:4]([CH2:8][CH2:9][CH3:10])C(O)=O)[CH3:3].S(Cl)(Cl)=O.[CH3:15][NH:16][C:17]1[C:22]([C:23]([NH2:25])=[O:24])=[C:21]([O:26][CH3:27])[C:20]([O:28][CH3:29])=[CH:19][CH:18]=1.Cl[CH:31](Cl)Cl>>[CH3:1][N:2]([CH3:3])[CH2:4][CH2:8][CH2:9][CH2:10][C:15]1[N:16]([CH3:31])[C:17]2[C:22]([C:23](=[O:24])[N:25]=1)=[C:21]([O:26][CH3:27])[C:20]([O:28][CH3:29])=[CH:19][CH:18]=2

Participants

5

Reactant 4

HCID 6212ChloroformHCID 24386Thionyl ChlorideHCID 178834622-(Dimethylamino)pentanoic acidHCID 669909586-Methylamino-2,3-dimethoxybenzamide

Product 1

HCID 669913772-(4-Dimethylamino-butyl)-5,6-dimethoxy-1-methyl-1H-quinazoline-4-one

Conditions

Temperature
57.5 °C

Procedure

3.80 g (20.9 mmol) Dimethylamino-pentanoic acid were added to 25 ml thionyl chloride and stirred for 90 min. at 55-60° C. The remaining thionyl chloride was distilled in vacuum and the residue was added to a solution of 2.00 g (11.1 mmol) 6-methylamino-2,3-dimethoxybenzamide dissolved in 30 ml trichloromethane at 0° C. The mixture was boiled for 2 h and stirred overnight at room temperature. After filtration the residue was dissolved in trichloromethane and saturated sodium bicarbonate solution. The organic solution was dried over magnesium sulfate and evaporated under vacuum.

Workup

  1. distillationThe remaining thionyl chloride was distilled in vacuum
  2. waitThe mixture was boiled for 2 h
  3. stirringstirred overnight at room temperature
  4. filtrationAfter filtration the residue
  5. dissolutionwas dissolved in trichloromethane
  6. dry with materialThe organic solution was dried over magnesium sulfate
  7. customevaporated under vacuum

Sources & evidence

ORD record
ord-1a77a7c056f24f0d8f7fce86aedb7dfd
Source dataset
uspto-grants-2011_11
Patent number
US08058431B2

Reaction notes

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