Chloroacetyl chloride → 5-Chloro-2-chloromethyl-3-(2-methoxyphenyl)-3H-quinazolin-4-one

HRID 1058891Notes

Reaction equation

HRID 1058891 reaction equation
[NH2:1][C:2]1[CH:18]=[CH:17][CH:16]=[C:15]([Cl:19])[C:3]=1[C:4]([NH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[O:13][CH3:14])=[O:5].[Cl:20][CH2:21][C:22](Cl)=O>C(O)(=O)C>[Cl:19][C:15]1[CH:16]=[CH:17][CH:18]=[C:2]2[C:3]=1[C:4](=[O:5])[N:6]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[O:13][CH3:14])[C:22]([CH2:21][Cl:20])=[N:1]2

Participants

4

Reactant 2

HCID 6577Chloroacetyl chlorideHCID 223165492-amino-6-chloro-N-(2-methoxyphenyl)benzamide

Product 1

HCID 223165905-Chloro-2-chloromethyl-3-(2-methoxyphenyl)-3H-quinazolin-4-oneYield 28%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Prepared according to Procedure B with 1l (2.6 g, 9.41 mmol) and chloroacetyl chloride (2.2 mL, 28.2 mmol) in acetic acid (40 mL). Purified by chromatography in CH2Cl2, followed by recrystallization from isopropanol to afford 874 mg of a pale yellow solid (28%). 1H NMR (CDCl3) δ: 7.55-7.74 (m, 2H); 7.47-7.54 (m, 2H); 7.34 (dd, J=1.7, 7.8 Hz, 1H); 7.13 (dt, J=1.2, 7.7 Hz, 1H); 7.08 (dd, J=1.0, 8.4 Hz, 1H); 4.29 (d, J=12 Hz, 1H); 4.11 (d, J=12 Hz, 1H); 3.80 (s, 3H). MS (ES): m/z 335.0 (M+).

Workup

  1. customPrepared
  2. customPurified by chromatography in CH2Cl2
  3. customfollowed by recrystallization from isopropanol

Sources & evidence

ORD record
ord-e5e76e5a8c474ea088a04cf7b6e3ff0b
Source dataset
uspto-grants-2003_02
Patent number
US06518277B1

Reaction notes

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