Chloroacetyl chloride → 2-Chloromethyl-3-(2-chlorophenyl)-5-methyl-3H-quinazolin-4-one

HRID 241909

Reaction equation

HRID 241909 reaction equation
[NH2:1][C:2]1[CH:17]=[CH:16][CH:15]=[C:14]([CH3:18])[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:19][CH2:20][C:21](Cl)=O>C(O)(=O)C>[Cl:19][CH2:20][C:21]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][CH:16]=[CH:15][C:14]=2[CH3:18])[N:1]=1

Participants

4

Reactant 2

HCID 6577Chloroacetyl chlorideHCID 167856852-Amino-N-(2-chlorophenyl)-6-methylbenzamide

Product 1

HCID 223165472-Chloromethyl-3-(2-chlorophenyl)-5-methyl-3H-quinazolin-4-oneYield 24%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Prepared according to Procedure B with 1g (2.18 g, 8.36 mmol) and chloroacetyl chloride (2.0 mL, 25.1 mmol) in acetic acid (40 mL). Purified by two chromatographies in CH2Cl2 and EtOAc/hexanes, followed by recrystallization from isopropanol to afford 638 mg of an off-white crystalline solid (24%). 1H NMR (DMSO-d6) δ: 7.73-7.80 (m, 3H); 7.58-7.64 (m, 3H); 7.41 (d, J=7.4 Hz, 1H); 4.40 (d, J=12 Hz, 1H), 4.26 (d, J=12 Hz, 1H); 2.74 (s, 3H). MS (ES): m/z 319.0 (M+).

Workup

  1. customPrepared
  2. customPurified by two chromatographies in CH2Cl2
  3. customEtOAc/hexanes, followed by recrystallization from isopropanol

Sources & evidence

ORD record
ord-bf1e06f4a1d04eedbca49bc95252282c
Source dataset
uspto-grants-2014_02
Patent number
US08653077B2

Linked notes

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