Chloroacetyl chloride → 5-Chloro-2-chloromethyl-3-o-tolyl-3H-quinazolin-4-one

HRID 452908

Reaction equation

HRID 452908 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[CH3:13])=[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[CH3:13])[C:21]([CH2:20][Cl:19])=[N:1]2

Participants

4

Reactant 2

HCID 6577Chloroacetyl chlorideHCID 124873672-Amino-6-chloro-N-o-tolylbenzamide

Product 1

HCID 124873735-Chloro-2-chloromethyl-3-o-tolyl-3H-quinazolin-4-oneYield 37%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Prepared according to Procedure B with 1j (750 mg, 2.88 mmol) and chloroacetyl chloride (0.69 mL, 8.63 mmol) in acetic acid (15 mL). Purified by chromatography in CH2Cl2, followed by recrystallization from isopropanol to afford 340 mg of a white solid (37%). 1H NMR (CDCl3) δ: 7.69 (d, J=2.1 Hz, 1H); 7.68 (q, J=7.4 Hz, 1H); 7.54 (dd, J=2.2, 7.0 Hz, 1H); 7.35-7.47 (m, 3H); 7.21-7.25 (m, 1H); 4.27 (d, J=12 Hz, 1H); 4.11 (d, J=12 Hz, 1H); 2.18 (s, 3H). MS (ES): m/z 319.0 (M+).

Workup

  1. customPrepared
  2. customPurified by chromatography in CH2Cl2
  3. customfollowed by recrystallization from isopropanol

Sources & evidence

ORD record
ord-ef8cdc8aa52741e7a7b3ea5820a2dd1d
Source dataset
uspto-grants-2013_07
Patent number
US08492389B2

Linked notes

Loading…