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

HRID 1458906Notes

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

Powdered aluminium chloride (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 mixture was stirred at 100° C. for 2 hours. The reaction mixture was poured into water, and the resulting mixture was extracted with chloroform. The chloroform layer was washed with water and dried over magnesium sulfate. The solvent was evaporated. The residue was subjected to column chromatography on silica gel. The fractions eluted with chloroform/ethyl acetate (=10/1, v/v) gave 2-chloromethyl-6,7-dimethoxy-4-(3,4-dimethoxyphenyl)quinazoline (4.9 g, 52%) which was then recrystallized from acetone.

Workup

extractionthe resulting mixture was extracted with chloroform
washThe chloroform layer was washed with water
dry with materialdried over magnesium sulfate
customThe solvent was evaporated
washThe fractions eluted with chloroform/ethyl acetate (=10/1

Sources & evidence

ORD record: ord-c471316ba44c44269b725ab518844426
Source dataset: uspto-grants-1998_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05852039

Reaction notes

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