Urea → 4-(3-Cyanophenyl)-1H-benzo[h]quinazolin-2-one

HRID 1191305Notes

Reaction equation

HRID 1191305 reaction equation
[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[C:12]([C:14]1[CH:15]=[C:16]([CH:19]=[CH:20][CH:21]=1)[C:17]#[N:18])=O.[NH2:22][C:23](N)=[O:24]>C(O)(=O)C>[C:17]([C:16]1[CH:15]=[C:14]([C:12]2[C:3]3[C:2](=[C:11]4[CH:10]=[CH:9][CH:8]=[CH:7][C:6]4=[CH:5][CH:4]=3)[NH:1][C:23](=[O:24])[N:22]=2)[CH:21]=[CH:20][CH:19]=1)#[N:18]

Participants

4

Reactant 2

HCID 1176UreaHCID 866904473-(1-Amino-2-naphthoyl)benzonitrile

Product 1

HCID 566506744-(3-Cyanophenyl)-1H-benzo[h]quinazolin-2-oneYield 60%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 3-(1-amino-2-naphthoyl)benzonitrile (200 mg, 0.734 mmol) in acetic acid (2 mL) was added urea (132 mg, 2.20 mmol). The mixture was heated under reflux for 18 hours. The reaction mixture was cooled to room temperature, and filtered. The obtained crystal was washed with ethyl acetate, and dried to give the titled compound as a yellow crystal (130 mg, yield 60%).

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 18 hours
  3. filtrationfiltered
  4. washThe obtained crystal was washed with ethyl acetate
  5. customdried

Sources & evidence

ORD record
ord-82810ac28de44b269b769ff83e3c9f82
Source dataset
uspto-grants-2014_03
Patent number
US08680110B2

Reaction notes

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