HCID 22648055, compound → 5-(2-chlorophenyl)-1-(2,6-dichlorophenyl)-7-nitro-3,4-dihydroquinazolin-2(1H)-one

HRID 394190Notes

Reaction equation

HRID 394190 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:17]=[C:16]([N+:18]([O-:20])=[O:19])[CH:15]=[C:14]2[C:9]=1[CH2:10][N:11](CC1C=CC(OC)=CC=1)[C:12](=[O:29])[N:13]2[C:21]1[C:26]([Cl:27])=[CH:25][CH:24]=[CH:23][C:22]=1[Cl:28]>FC(F)(F)C(O)=O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:17]=[C:16]([N+:18]([O-:20])=[O:19])[CH:15]=[C:14]2[C:9]=1[CH2:10][NH:11][C:12](=[O:29])[N:13]2[C:21]1[C:26]([Cl:27])=[CH:25][CH:24]=[CH:23][C:22]=1[Cl:28]

Participants

3

Reactant 1

HCID 22648055HCID 22648055, compound

Product 1

HCID 226481565-(2-chlorophenyl)-1-(2,6-dichlorophenyl)-7-nitro-3,4-dihydroquinazolin-2(1H)-one

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 5-(2-chlorophenyl)-1-(2,6-dichlorophenyl)-3-(4-methoxybenzyl)-7-nitro-3,4-dihydroquinazolin-2(1H)-one (32 mg, 0.56 mmol) in 1 mL trifluoroacetic acid was stirred at 95° C. for 1.25 h. The solvent was removed under reduced pressure and the product was purified by preparative thin-layer chromatography, eluting with 93:7 CH2Cl2-methanol to yield 5-(2-chlorophenyl)-1-(2,6-dichlorophenyl)-7-nitro-3,4-dihydroquinazolin-2(1H)-one. Mass spectrum (ESI) 448 (M+1). 1H NMR (500 MHz, CDCl3): δ 3.35 (½ ABq, J=15.5 Hz, 1H); 3.52 (½ ABq, J=15.5 Hz. 1H); 7.00 (s, 1H); 7.32 (d, J=2.1 Hz, 1H); 7.46 (m, 3H); 7.58 (m, 3H); 7.81 (s, 1H).

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe product was purified by preparative thin-layer chromatography
  3. washeluting with 93:7 CH2Cl2-methanol

Sources & evidence

ORD record
ord-b7962b7f6e3f4a629a1907e8e8e57ffc
Source dataset
uspto-grants-2004_10
Patent number
US06809199B2

Reaction notes

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