1,1,1-Trimethoxy-2-chloroethane → 2-chloromethyl-7-(3-trifluoromethyl-pyridin-2-yl)-3H-quinazolin-4-one

HRID 968612Notes

Reaction equation

HRID 968612 reaction equation
[NH2:1][C:2]1[CH:10]=[C:9]([C:11]2[C:16]([C:17]([F:20])([F:19])[F:18])=[CH:15][CH:14]=[CH:13][N:12]=2)[CH:8]=[CH:7][C:3]=1[C:4]([NH2:6])=[O:5].[Cl:21][CH2:22][C:23](OC)(OC)OC>>[Cl:21][CH2:22][C:23]1[NH:6][C:4](=[O:5])[C:3]2[C:2](=[CH:10][C:9]([C:11]3[C:16]([C:17]([F:20])([F:18])[F:19])=[CH:15][CH:14]=[CH:13][N:12]=3)=[CH:8][CH:7]=2)[N:1]=1

Participants

3

Reactant 2

HCID 1447021,1,1-Trimethoxy-2-chloroethaneHCID 220300742-Amino4-(3-trifluoromethyl-pyridin-2-yl)-benzamide

Product 1

HCID 1356820662-chloromethyl-7-(3-trifluoromethyl-pyridin-2-yl)-3H-quinazolin-4-one

Procedure

Heat a solution of 2-amino-4-(3-trifluoromethyl-pyridin-2-yl)-benzamide (100 mg, 0.356 mmol) in 2-chloro-1,1,1-trimethoxyethane (bp 138° C.) at 130° C. for 4 hours. Concentrate the mixture under reduced pressure to give 2-chloromethyl-7-(3-trifluoromethyl-pyridin-2-yl)-3H-quinazolin-4-one as an oil which crystallizes on standing.

Workup

  1. concentrationConcentrate the mixture under reduced pressure

Sources & evidence

ORD record
ord-aa2d01f2aee94601afe34045c4fa8c66
Source dataset
uspto-grants-2007_12
Patent number
US07304059B2

Reaction notes

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