Water → 2-amino-7-(4-chlorophenyl)-7,8-dihydroquinazolin-5(6H)-one

HRID 2046451Notes

Reaction equation

HRID 2046451 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:13][C:12](=O)[C:11](=[CH:15]N(C)C)[C:10](=[O:19])[CH2:9]2)=[CH:4][CH:3]=1.Cl.[NH2:21][C:22]([NH2:24])=[NH:23].C(=O)([O-])[O-].[Na+].[Na+].O>C(O)C>[NH2:23][C:22]1[N:24]=[CH:15][C:11]2[C:10](=[O:19])[CH2:9][CH:8]([C:5]3[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=3)[CH2:13][C:12]=2[N:21]=1

Participants

6

Reactant 4

HCID 962WaterHCID 5742Guanidine HydrochlorideHCID 10340Sodium CarbonateHCID 5670705-(4-Chlorophenyl)-2-[(dimethylamino)methylene]-1,3-cyclohexanedione

Product 1

HCID 27723712-amino-7-(4-chlorophenyl)-7,8-dihydroquinazolin-5(6H)-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

5-(4-Chloro-phenyl)-2-dimethylaminomethylene-cyclohexane-1,3-dione (0.8 g, 2.89 mmol) from stage 1, guanidine hydrochloride (551 mg, 5.77 mmol) and sodium carbonate (919 mg, 8.67 mmol) were stirred in ethanol (10 ml) at reflux for 4 h. The reaction mixture was cooled to ambient temperature and water (10 ml) was added to the flask. The resulting precipitate was recovered by filtration, washed with water (15 ml), heptane (15 ml) and air dried.

Workup

  1. temperatureat reflux for 4 h
  2. filtrationThe resulting precipitate was recovered by filtration
  3. washwashed with water (15 ml), heptane (15 ml) and air
  4. customdried

Sources & evidence

ORD record
ord-e209105160994304acc27b198ef271aa
Source dataset
uspto-grants-2013_11
Patent number
US08592430B2

Reaction notes

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