Chloroacetyl chloride → 8-Chloro-2-chloromethyl-3-(2-chlorophenyl)-3H-quinazolin-4-one

HRID 467901Notes

Reaction equation

HRID 467901 reaction equation
[NH2:1][C:2]1[C:17]([Cl:18])=[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:19][CH2:20][C:21](Cl)=O>C(O)(=O)C>[Cl:18][C:17]1[CH:16]=[CH:15][CH:14]=[C:3]2[C:2]=1[N:1]=[C:21]([CH2:20][Cl:19])[N:6]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[Cl:13])[C:4]2=[O:5]

Participants

4

Reactant 2

HCID 6577Chloroacetyl chlorideHCID 223165852-amino-3-chloro-N-(2-chlorophenyl)benzamide

Product 1

HCID 223165848-Chloro-2-chloromethyl-3-(2-chlorophenyl)-3H-quinazolin-4-oneYield 74.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Prepared according to Procedure B with 1h (500 mg, 1.78 mmol) and chloroacetyl chloride (0.49 mL, 6.13 mmol) in acetic acid (10 mL). Purified by extraction from aqueous K2CO3, followed by recrystallization from isopropanol to afford 448 mg of a yellow solid (74%). 1H NMR (CDCl3) δ: 8.23 (dd, J=1.4, 8.0 Hz, 1H); 7.90 (dd, J=1.4, 7.8 Hz, 1H); 7.61-7.66 (m, 1H); 7.51-7.55 (m, 3H); 7.47 (t, J=8.0 Hz, 1H); 4.48 (d, J=12 Hz, 1H), 4.12 (d, J=12 Hz, 1H). MS (ES): m/z 339.0 (M+).

Workup

  1. customPrepared
  2. customPurified by extraction from aqueous K2CO3
  3. customfollowed by recrystallization from isopropanol

Sources & evidence

ORD record
ord-b7b8704fb56841309becab0b64f96356
Source dataset
uspto-grants-2014_01
Patent number
US08623881B2

Reaction notes

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