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

HRID 1095624Notes

Reaction equation

HRID 1095624 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-7fbe4c985d8042159927c85e7f913b00
Source dataset
uspto-grants-2012_03
Patent number
US08138195B2

Reaction notes

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