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

HRID 433246Notes

Reaction equation

HRID 433246 reaction equation
[NH2:1][C:2]1[CH:17]=[CH:16][CH:15]=[C:14]([Cl: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:18][C:14]1[CH:15]=[CH:16][CH:17]=[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[Cl:13])[C:21]([CH2:20][Cl:19])=[N:1]2

Participants

4

Reactant 2

HCID 6577Chloroacetyl chlorideHCID 223165862-amino-6-chloro-N-(2-chlorophenyl)benzamide

Product 1

HCID 223165715-Chloro-2-chloromethyl-3-(2-chlorophenyl)-3H-quinazolin-4-oneYield 65.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Prepared according to Procedure B with 1f (1.00 g, 3.56 mmol) and chloroacetyl chloride (0.85 mL, 10.7 mmol) in acetic acid (15 mL). Purified by recrystallization from isopropanol to afford 791 mg of an off-white crystalline solid (65%). 1H NMR (CDCl3) δ: 7.70 (s, 1H); 7.68 (d, J=3.8 Hz, 1H); 7.61-7.65 (m, 1H); 7.55 (dd, J=2.7, 6.4 Hz, 1H); 7.51 (d, J=3.1 Hz, 1H); 7.50 (s, 2H); 4.35 (d, J=12 Hz, 1H), 4.05 (d, J=12 Hz, 1H). MS (ES): m/z 339.0 (M+).

Workup

  1. customPrepared
  2. customPurified by recrystallization from isopropanol

Sources & evidence

ORD record
ord-7a7520ff437541dab5b3476c95ec3efe
Source dataset
uspto-grants-2003_12
Patent number
US06667300B2

Reaction notes

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