4-Bromophenyl isothiocyanate → 1-(p-Bromophenyl)-3-(3,4-dihydro-4-oxo-3-quinazolinyl)-2-thiourea

HRID 1197447Notes

Reaction equation

HRID 1197447 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]=[C:9]=[S: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>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([NH:11][N:12]2[C:21](=[O:22])[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[N:14]=[CH:13]2)=[S:10])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 161334-Bromophenyl isothiocyanateHCID 631253-Amino-4(3H)-quinazolinone

Product 1

HCID 157667041-(p-Bromophenyl)-3-(3,4-dihydro-4-oxo-3-quinazolinyl)-2-thiourea

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

4-Bromophenyl isothiocyanate (2.51 g, 11.72 mmol) is added to a mixture of 3-amino-4(3H)quinazolinone (1.72 g, 10.66 mmol) in a 1,2-dichloroethane at reflux under a nitrogen atmosphere. The reaction mixture is heated at reflux for 2 days, cooled, washed with ether and filtered. The filter cake is dried to give the title product as a white solid, 2.44 g, mp 189°-190° C.

Workup

  1. temperatureat reflux under a nitrogen atmosphere
  2. temperatureThe reaction mixture is heated
  3. temperatureat reflux for 2 days
  4. temperaturecooled
  5. washwashed with ether
  6. filtrationfiltered
  7. customThe filter cake is dried

Sources & evidence

ORD record
ord-2772e12dde9846c1878c2e277a31d6d1
Source dataset
uspto-grants-1994_01
Patent number
US05276038

Reaction notes

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