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

HRID 1058880Notes

Reaction equation

HRID 1058880 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-cd6944cf36a34d4fa320ef85e5ef566b
Source dataset
uspto-grants-2003_02
Patent number
US06518277B1

Reaction notes

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