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

HRID 1095625Notes

Reaction equation

HRID 1095625 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-4f828eed1fca40b9a2309e8a99b0373d
Source dataset
uspto-grants-2012_03
Patent number
US08138195B2

Reaction notes

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