Chloranil → HCID 23085645, compound

HRID 2243093Notes

Reaction equation

HRID 2243093 reaction equation
[C:1]1([C:7]2[NH:16][CH2:15][C:14]3[C:9](=[CH:10][CH:11]=[C:12]([N+:17]([O-:19])=[O:18])[CH:13]=3)[N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1(Cl)C(=O)C(Cl)=C(Cl)C(=O)C=1Cl>C1(C)C=CC=CC=1>[C:1]1([C:7]2[N:16]=[CH:15][C:14]3[C:9](=[CH:10][CH:11]=[C:12]([N+:17]([O-:19])=[O:18])[CH:13]=3)[N:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 8371ChloranilHCID 178526438HCID 178526438, compound

Product 1

HCID 23085645HCID 23085645, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

2-Phenyl-6-nitro-3,4-dihydroquinazoline (27 g, 0.106 mol) and chloranil (32.4 g, 0.13 mol) in toluene (450 ml) are refluxed for 60 minutes. The mixture is cooled to room temperature, and the precipitate is filtered off and washed with toluene (350 ml). The filtrate is suspended in 0.5N NaOH (400 ml) and the aqueous phase is extracted with dichloromethane (100 ml). The combined organic phases are washed with water and concentrated. The solid is recrystallized from hexane. Yield: 8.8 g (34%); Rf (8/2 petroleum ether/ethyl acetate): 0.71; 1H-NMR (d6-DMSO) 9.91 (s, 1H); 9.18 (d, 1H); 8.61 (m, 3H); 8.24 (d, 1H); 7.55 (m, 3H).

Workup

  1. filtrationthe precipitate is filtered off
  2. washwashed with toluene (350 ml)
  3. extractionthe aqueous phase is extracted with dichloromethane (100 ml)
  4. washThe combined organic phases are washed with water
  5. concentrationconcentrated
  6. customThe solid is recrystallized from hexane

Sources & evidence

ORD record
ord-25c0a033860d42c8b66c02b1a327cfe6
Source dataset
uspto-grants-2010_03
Patent number
US07674809B2

Reaction notes

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