Chloroacetyl chloride → 2-Chloromethyl-3-(2-chlorophenyl)-6,7-dimethoxy-3H-quinazolin-4-one

HRID 241904

Reaction equation

HRID 241904 reaction equation
[NH2:1][C:2]1[CH:17]=[C:16]([O:18][CH3:19])[C:15]([O:20][CH3:21])=[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](=[CH:17][C:16]([O:18][CH3:19])=[C:15]([O:20][CH3:21])[CH:14]=2)[N:1]=1

Participants

4

Reactant 2

HCID 6577Chloroacetyl chlorideHCID 141271432-amino-N-(2-chlorophenyl)-4,5-dimethoxybenzamide

Product 1

HCID 223165582-Chloromethyl-3-(2-chlorophenyl)-6,7-dimethoxy-3H-quinazolin-4-oneYield 46%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Prepared according to Procedure B with 1a (2.95 g, 9.63 mmol) and chloroacetyl chloride (2.3 mL, 28.9 mmol) in acetic acid (30 mL). Purified by extraction from aq. K2CO3 and recrystallization from isopropanol to afford 1.61 g of a brown crystalline solid (46%). 1H NMR (CDCl3) δ: 7.59-7.66 (m, 2H); 7.45-7.56 (m, 3H); 7.20 (s, 1H); 4.37 (d, J=12 Hz, 1H), 4.08 (d, J=12 Hz, 1H); 4.04 (s, 3H); 4.00 (s, 3H). MS (ES): m/z 365.0 (M+).

Workup

  1. customPrepared
  2. customPurified by extraction from aq. K2CO3 and recrystallization from isopropanol

Sources & evidence

ORD record
ord-0c2482f9f2e64a4e9e013986a9ba96db
Source dataset
uspto-grants-2014_02
Patent number
US08653077B2

Linked notes

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