Chloroacetyl chloride → 2-Chloromethyl-3-(2-chlorophenyl)-5-fluoro-3H-quinazolin-4-one

HRID 392250

Reaction equation

HRID 392250 reaction equation
[NH2:1][C:2]1[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[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:19][CH2:20][C:21]1[N:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[Cl:13])[C:4](=[O:5])[C:3]2[C:2](=[CH:17][CH:16]=[CH:15][C:14]=2[F:18])[N:1]=1

Participants

4

Reactant 2

HCID 6577Chloroacetyl chlorideHCID 223165682-amino-N-(2-chlorophenyl)-6-fluorobenzamide

Product 1

HCID 223165672-Chloromethyl-3-(2-chlorophenyl)-5-fluoro-3H-quinazolin-4-oneYield 70.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Prepared according to Procedure B with 1e (500 mg, 1.89 mmol) and chloroacetyl chloride (0.45 mL, 5.67 mmol) in acetic acid (10 mL). Purified by extraction from aq. K2CO3 and recrystallization from isopropanol to afford 430 mg of an off-white crystalline solid (70%). 1H NMR (CDCl3) δ: 7.76 (dt, J=5.3, 8.2 Hz, 1H); 7.56-7.65 (m, 2H); 7.47-7.56 (m, 3H); 7.16-7.25 (m, 1H); 4.35 (d, J=12 Hz, 1H), 4.07 (d, J=12 Hz, 1H). MS (ES): m/z 323.0 (M+).

Workup

  1. customPrepared
  2. customPurified by extraction from aq. K2CO3 and recrystallization from isopropanol

Sources & evidence

ORD record
ord-3b0a524a1ffd43e08078f47e58d89b15
Source dataset
uspto-grants-2004_10
Patent number
US06800620B2

Linked notes

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