2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 136364497, compound

HRID 1469213Notes

Reaction equation

HRID 1469213 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[CH:9]1[NH:18][C:17](=[O:19])[C:16]2[C:11](=[C:12]([CH3:20])[CH:13]=[CH:14][CH:15]=2)[NH:10]1.ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl>C(O)C>[Cl:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[C:9]1[NH:18][C:17](=[O:19])[C:16]2[C:11](=[C:12]([CH3:20])[CH:13]=[CH:14][CH:15]=2)[N:10]=1

Participants

4

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 67971766HCID 67971766, compound

Product 1

HCID 136364497HCID 136364497, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-(2-Chloro-4-methylphenyl)-8-methyl-2,3-dihydroquinazolin-4(1H)-one (159 mg, 0.6 mmol) and 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (126 mg, 0.6 mmol) were dissolved in 5 ml of ethanol and then stirred at room temperature for 2 hours. The reaction mixture was filtered and the solid was washed with a little ethanol. This gave 108 mg (65.5% of theory) of 2-(2-chloro-4-methylphenyl)-8-methylquinazolin-4(3H)-one as a colorless said of melting point 234° C. 1H NMR (400 MHz, d6-DMSO δ, ppm) 12.54 (br. S, 1H), 8.00 (d, 1H), 7.70 (d, 1H), 7.56 (d, 1H), 7.42 (m, 2H), 7.30 (d, 1H), 2.51 (s, 3H), 2.40 (s, 3H).

Workup

  1. filtrationThe reaction mixture was filtered
  2. washthe solid was washed with a little ethanol

Sources & evidence

ORD record
ord-56fdaf1958694fdda8789673a148d6c0
Source dataset
uspto-grants-2015_04
Patent number
US09006265B2

Reaction notes

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