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

HRID 392252Notes

Reaction equation

HRID 392252 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-30a869bffae747919eb307a54087f2b3
Source dataset
uspto-grants-2004_10
Patent number
US06800620B2

Reaction notes

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