1,1,1-Trimethoxy-2-chloroethane → 7-Bromo-2-(chloromethyl)quinazolin-4-ol

HRID 968603Notes

Reaction equation

HRID 968603 reaction equation
[NH2:1][C:2]1[CH:10]=[C:9]([Br:11])[CH:8]=[CH:7][C:3]=1[C:4]([NH2:6])=[O:5].[Cl:12][CH2:13][C:14](OC)(OC)OC>>[Br:11][C:9]1[CH:10]=[C:2]2[C:3]([C:4](=[O:5])[NH:6][C:14]([CH2:13][Cl:12])=[N:1]2)=[CH:7][CH:8]=1

Participants

3

Reactant 2

HCID 1447021,1,1-Trimethoxy-2-chloroethaneHCID 138055072-Amino-4-bromobenzamide

Product 1

HCID 1356820607-Bromo-2-(chloromethyl)quinazolin-4-ol

Procedure

Reflux a solution of 2-amino-4-bromobenzamide (27 g, 0.13 mol; see Joshi and Chaudhari, (1987) Indian J. Chem., Sect. B, 26B(6):602–4) in 2-chloro-1,1,1-trimethoxyethane (50 mL) for 30 minutes, during which time a large precipitate appears. Evaporate the mixture fully and triturate with ether to collect 28 g of 7-bromo-2-chloromethyl-3H-quinazolin-4-one as a white solid.

Workup

  1. customEvaporate the mixture fully
  2. customtriturate with ether
  3. customto collect 28 g of 7-bromo-2-chloromethyl-3H-quinazolin-4-one as a white solid

Sources & evidence

ORD record
ord-f1bbec51053947648dfc42c441691c0a
Source dataset
uspto-grants-2007_12
Patent number
US07304059B2

Reaction notes

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