3-Amino-4(3H)-quinazolinone → 1-(3,4-Dihydro-4-oxo-3-quinazolinyl)-3-(p-fluorophenyl)urea

HRID 1197446Notes

Reaction equation

HRID 1197446 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]=[C:9]=[O:10])=[CH:4][CH:3]=1.[NH2:11][N:12]1[C:21](=[O:22])[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[N:14]=[CH:13]1>ClCCCl>[O:22]=[C:21]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[N:14]=[CH:13][N:12]1[NH:11][C:9]([NH:8][C:5]1[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=1)=[O:10]

Participants

4

Reactant 2

HCID 631253-Amino-4(3H)-quinazolinoneHCID 709554-Fluorophenyl isocyanate

Product 1

HCID 189619001-(3,4-Dihydro-4-oxo-3-quinazolinyl)-3-(p-fluorophenyl)urea

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
0 °C

Procedure

4-Fluorophenyl isocyanate (0.74 mL, 6.51 mmol) is added to a mixture of 3-amino-4(3H)-quinazolinone (1.00 g, 6.21 mmol) in 1,2-dichloroethane at reflux. The reaction mixture is heated at reflux for 18 hours, cooled to 0° C. and filtered. The filter cake is washed with ether and dried to give the title product as a white solid, 1.64 g (89%), mp 237°-238° C.

Workup

  1. temperatureat reflux
  2. temperatureThe reaction mixture is heated
  3. temperatureat reflux for 18 hours
  4. filtrationfiltered
  5. washThe filter cake is washed with ether
  6. customdried

Sources & evidence

ORD record
ord-1e5a37460c44453194c55b4de99d7b6d
Source dataset
uspto-grants-1994_01
Patent number
US05276038

Reaction notes

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