Chloroacetyl chloride → 2-Chloromethyl-3-(2-chlorophenyl)-8-trifluoromethyl-3H-quinazolin-4-one

HRID 452911Notes

Reaction equation

HRID 452911 reaction equation
[NH2:1][C:2]1[C:17]([C:18]([F:21])([F:20])[F:19])=[CH:16][CH:15]=[CH:14][C:3]=1[C:4]([NH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[Cl:13])=[O:5].[Cl:22][CH2:23][C:24](Cl)=O>C(O)(=O)C>[Cl:22][CH2:23][C:24]1[N:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[Cl:13])[C:4](=[O:5])[C:3]2[C:2](=[C:17]([C:18]([F:21])([F:19])[F:20])[CH:16]=[CH:15][CH:14]=2)[N:1]=1

Participants

4

Reactant 2

HCID 6577Chloroacetyl chlorideHCID 223165782-Amino-N-(2-chlorophenyl)-3-trifluoromethylbenzamide

Product 1

HCID 223165502-Chloromethyl-3-(2-chlorophenyl)-8-trifluoromethyl-3H-quinazolin-4-oneYield 61%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Prepared according to Procedure B with 1m (500 mg, 1.59 mmol) and chloroacetyl chloride (0.38 mL, 4.77 mmol) in acetic acid (10 mL). Purified by recrystallization from isopropanol to afford 359 mg of a white crystalline solid (61%). 1H NMR (CDCl3) δ: 8.51 (dd, J=1.0, 8.0 Hz, 1H); 8.14 (d, J=7.3 Hz, 1H); 7.65 (dd, J=2.5, 5.6 Hz, 1H); 7.62 (d, J=3.9 Hz, 1H); 7.48-7.60 (m, 3H); 4.44 (d, J=12 Hz, 1H), 4.12 (d, J=12 Hz, 1H). MS (ES): m/z 373.0 (M+).

Workup

  1. customPrepared
  2. customPurified by recrystallization from isopropanol

Sources & evidence

ORD record
ord-7f14a5b22c54433abb0d8e50afb0cbe2
Source dataset
uspto-grants-2013_07
Patent number
US08492389B2

Reaction notes

Loading…