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

HRID 1095626Notes

Reaction equation

HRID 1095626 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-1d0628fd3666456e86f2fb33b9c49b2f
Source dataset
uspto-grants-2012_03
Patent number
US08138195B2

Reaction notes

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