Methyl Isocyanate → 6-chloro-4-hydroxy-3-methyl-4-phenyl-1H-quinazolin-2-one

HRID 128023Notes

Reaction equation

HRID 128023 reaction equation
[NH2:1][C:2]1[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:5].[CH3:17][N:18]=[C:19]=[O:20]>C(Cl)Cl>[Cl:16][C:13]1[CH:12]=[C:3]2[C:2](=[CH:15][CH:14]=1)[NH:1][C:19](=[O:20])[N:18]([CH3:17])[C:4]2([OH:5])[C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

Participants

4

Reactant 2

HCID 12228Methyl IsocyanateHCID 128702-Amino-5-chlorobenzophenone

Product 1

HCID 3200296-chloro-4-hydroxy-3-methyl-4-phenyl-1H-quinazolin-2-oneYield 96.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 100 g (0.43 mole) of 2-amino-5-chlorobenzophenone and 40 g (0.7 mole) of methyl isocyanate in 300 ml of methylene chloride was refluxed for two days and then cooled. The solid portion of the reaction mixture was collected on a filter and washed with methylene chloride to give 119.8 g (96% yield) of 6-chloro-3,4-dihydro-4-hydroxy-3-methyl-4-phenyl-2(1H)-quinazolinone as a white crystalline powder: mp 296°-298° (dec); 1H nmr (DMSO-d6), δ 2.66 ppm (s, 3H), 6.8-7.6 ppm (m, 8H) and 10.0 ppm (s, NH); 13C nmr (DMSO-d6) δ 86.6 ppm (for COH) and 151.4 ppm (for NHCO).

Workup

  1. temperaturecooled
  2. customThe solid portion of the reaction mixture was collected on
  3. filtrationa filter
  4. washwashed with methylene chloride

Sources & evidence

ORD record
ord-0f28cc6b24b24e7e95b5b92dff074ccc
Source dataset
uspto-grants-1981_03
Patent number
US04258187

Reaction notes

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