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

HRID 1584142Notes

Reaction equation

[NH2:1][C:2]1[CH:19]=[C:18]([O:20][CH3:21])[C:17]([O:22][CH3:23])=[CH:16][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[C:8]([O:14][CH3:15])[CH:7]=1)=O.[Cl:24][CH2:25][C:26]#[N:27].[Cl-].[Al+3].[Cl-].[Cl-]>O>[Cl:24][CH2:25][C:26]1[N:27]=[C:4]([C:6]2[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[C:8]([O:14][CH3:15])[CH:7]=2)[C:3]2[C:2](=[CH:19][C:18]([O:20][CH3:21])=[C:17]([O:22][CH3:23])[CH:16]=2)[N:1]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a mixture of 2-amino-4,5,3',4'-tetramethoxybenzophenone (8.0 g) and chloroacetonitrile (25 ml), powdered aluminum chloride (6.7 g) was added, followed by stirring at 100° C. for 2 hours. The reaction mixture was poured over water and extracted with chloroform. The chloroform layer was washed with water and dried (MgSO4), after which the solvent was distilled off. The residue was subjected to silica gel column chromatography and eluted with chloroform-ethyl acetate (10:1, v/v) to yield 2-chloromethyl-6,7-dimethoxy-4-(3,4-dimethoxyphenyl)quinazoline (4.9 g, 52%), which was then recrystallized from acetone to yield a colorless prismatic crystal having a melting point of 183 to 184° C.

Workup

additionwas added
extractionextracted with chloroform
washThe chloroform layer was washed with water
dry with materialdried (MgSO4)
distillationafter which the solvent was distilled off
washeluted with chloroform-ethyl acetate (10:1

Sources & evidence

ORD record: ord-443de1da017b40d8befe2fc158f8a699
Source dataset: uspto-grants-1999_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05932592

Reaction notes

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