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

HRID 433248Notes

Reaction equation

HRID 433248 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-b0db2a5df3bd46f486931f80d9b11870
Source dataset
uspto-grants-2003_12
Patent number
US06667300B2

Reaction notes

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