Chloroacetyl chloride → 3-Biphenyl-2-yl-5-chloro-2-chloromethyl-3H-quinazolin-4-one

HRID 497104Notes

Reaction equation

HRID 497104 reaction equation
[NH2:1][C:2]1[CH:22]=[CH:21][CH:20]=[C:19]([Cl:23])[C:3]=1[C:4]([NH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:5].[Cl:24][CH2:25][C:26](Cl)=O>C(O)(=O)C>[C:8]1([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=1[N:6]1[C:4](=[O:5])[C:3]2[C:2](=[CH:22][CH:21]=[CH:20][C:19]=2[Cl:23])[N:1]=[C:26]1[CH2:25][Cl:24]

Participants

4

Reactant 2

HCID 6577Chloroacetyl chlorideHCID 223165622-Amino-N-biphenyl-2-yl-6-chlorobenzamide

Product 1

HCID 223165793-Biphenyl-2-yl-5-chloro-2-chloromethyl-3H-quinazolin-4-oneYield 61%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Prepared according to Procedure B with 1i (2.0 g, 6.20 mmol) and chloroacetyl chloride (1.5 mL, 18.6 mmol) in acetic acid (30 mL). Purified by chromatography in CH2Cl21 followed by recrystallization from isopropanol to afford 1.44 g of an off-white solid (61%). 1H NMR (CDCl3) δ: 7.61-7.64 (m, 1H); 7.58-7.59 (m, 1H); 7.54-7.57 (m, 2H); 7.52-7.53 (m, 1H); 7.45-7.52 (m, 2H); 7.24 (s, 5H); 3.92-4.03 (m, 2H). MS (ES): m/z 381.0 (M+).

Workup

  1. customPrepared
  2. customPurified by chromatography in CH2Cl21
  3. customfollowed by recrystallization from isopropanol

Sources & evidence

ORD record
ord-9de664c1b6d14e1080dac5ffb8bcaf93
Source dataset
uspto-grants-2005_09
Patent number
US06949535B2

Reaction notes

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