Chloroacetonitrile → 2-Chloromethyl-4-(3,4-dimethoxyphenyl)-6,7-dimethoxyquinazoline

HRID 617215Notes

Reaction equation

[Cl-].[Al+3].[Cl-].[Cl-].[NH2:5][C:6]1[CH:23]=[C:22]([O:24][CH3:25])[C:21]([O:26][CH3:27])=[CH:20][C:7]=1[C:8]([C:10]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[C:12]([O:18][CH3:19])[CH:11]=1)=O.[Cl:28][CH2:29][C:30]#[N:31]>O>[Cl:28][CH2:29][C:30]1[N:31]=[C:8]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[C:12]([O:18][CH3:19])[CH:11]=2)[C:7]2[C:6](=[CH:23][C:22]([O:24][CH3:25])=[C:21]([O:26][CH3:27])[CH:20]=2)[N:5]=1

Participants

Conditions

Temperature: 100 °C

Procedure

Aluminum chloride powder (6.7 g) was added to a mixture of 2-amino-4,5,3',4'-tetramethoxybenzophenone (8.0 g) and chloroacetonitrile (25 ml), and the resulting mixture was stirred at 100° C. for 2 hours. The reaction mixture was poured into water and extracted with chloroform. The chloroform layer was washed with water and dried (MgSO4), and the solvent was distilled off under reduced pressure. The residue was subjected to column chromatography on silica gel. From the fraction eluted with chloroform/ethyl acetate (10:1, v/v), 2-chloromethyl-6,7-dimethoxy-4-(3,4-dimethoxyphenyl)quinazoline (4.9 g., 52%) was obtained and recrystallized from acetone. Colorless prisms. mp. 183-184° C.

Workup

extractionextracted with chloroform
washThe chloroform layer was washed with water
dry with materialdried (MgSO4)
distillationthe solvent was distilled off under reduced pressure
washFrom the fraction eluted with chloroform/ethyl acetate (10:1

Sources & evidence

ORD record: ord-79ada14b0c13468e8d040f17f5336309
Source dataset: uspto-grants-1999_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05948782

Reaction notes

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