Chloroacetyl chloride → 6-Bromo-2-chloromethyl-3-(2-chlorophenyl)-3H-quinazolin-4-one

Participants

Role	Name	HCID	Charge
Reactant	Chloroacetyl chloride	HCID 6577	—
Reactant	2-amino-5-bromo-N-(2-chlorophenyl)benzamide	HCID 22316548	—
Solvent	Acetic Acid	HCID 176	—
Product	6-Bromo-2-chloromethyl-3-(2-chlorophenyl)-3H-quinazolin-4-one	HCID 22316575	83%

Reaction Steps

Prepared according to Procedure B with 1b (500 mg, 1.54 mmol) and chloroacetyl chloride (0.37 mL, 4.61 mmol) in acetic acid (10 mL). Purified by recrystallization from isopropanol to afford 490 mg of an off-white solid (83%). 1H NMR (CDCl3) δ: 8.43 (d, J=2.3 Hz, 1H); 7.91 (dd, J=2.3, 8.7 Hz, 1H); 7.67 (d, J=8.7 Hz, 1H); 7.60-7.65 (m, 1H); 7.47-7.56 (m, 2H); 7.52 (t, J=5.3 Hz, 1H); 7.47-7.56 (m, 1H); 4.37 (d, J=12 Hz, 1H), 4.06 (d, J=12 Hz, 1H). MS (ES): m/z 385.0 (M+).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08637533B2
Source dataset	uspto-grants-2014_01
ORD ID	ord-cf04c4ebf8674e87951261fe0eecca5f
Source note	uspto-grants-2014_01