Ethyl isocyanate → 6-Chloro-3-ethyl-4-hydroxy-4-phenyl-3,4-dihydroquinazolin-2(1H)-one

HRID 128025Notes

Reaction equation

HRID 128025 reaction equation
[CH2:1]([N:3]=[C:4]=[O:5])[CH3:2].[NH2:6][C:7]1[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:8]=1[C:9]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:10]>C(Cl)Cl>[Cl:21][C:18]1[CH:17]=[C:8]2[C:7](=[CH:20][CH:19]=1)[NH:6][C:4](=[O:5])[N:3]([CH2:1][CH3:2])[C:9]2([OH:10])[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

4

Reactant 2

HCID 8022Ethyl isocyanateHCID 128702-Amino-5-chlorobenzophenone

Product 1

HCID 3198666-Chloro-3-ethyl-4-hydroxy-4-phenyl-3,4-dihydroquinazolin-2(1H)-oneYield 84%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 28.4 g (31.7 ml, 0.4 mole) of ethyl isocyanate and 46.3 g (0.2 mole) of 2-amino-5-chlorobenzophenone in 100 ml of methylene chloride was refluxed for 20 hr. The reaction mixture was cooled, and the solid portion was collected on a filter and washed with methylene chloride to give 50.72 g (84%) of 6-chloro-3-ethyl-3,4-dihydro-4-hydroxy-4-phenyl-2(1H)-quinazolinone as colorless crystals: mp 182°-184°; 13C nmr (DMSO-d6) δ 86.9 ppm (for COH) and δ 151.0 ppm (for NHCO).

Workup

  1. temperatureThe reaction mixture was cooled
  2. customthe solid portion was collected on
  3. filtrationa filter
  4. washwashed with methylene chloride

Sources & evidence

ORD record
ord-9beae0d045324be8afe97cc46f7190da
Source dataset
uspto-grants-1981_03
Patent number
US04258187

Reaction notes

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