Phosgene → 5-Chloro-2-phenyl-7,8,9,10-tetrahydro-1,2,4-triazolo[4,3-c]quinazolin-3-one
Reaction equation
[Cl:1][C:2]1[N:11]=[C:10](Cl)[C:9]2[CH2:8][CH2:7][CH2:6][CH2:5][C:4]=2[N:3]=1.[C:13]1([NH:19][NH2:20])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(N(CC)C(C)C)(C)C.[C:30](Cl)(Cl)=[O:31]>C1COCC1.O>[Cl:1][C:2]1[N:11]2[C:30](=[O:31])[N:19]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[N:20]=[C:10]2[C:9]2[CH2:8][CH2:7][CH2:6][CH2:5][C:4]=2[N:3]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
A mixture of 2,4-dichloro-5,6,7,8-tetrahydroquinazoline [prepared according to the procedure described by M. Botta et al., 40, Tetrahedron, (1984), 3313] (500 mg, 2.4 mmol), phenylhydrazine (270 mg, 2.5 mmol) and N,N-diisopropylethylamine (1 ml, 5.7 mmol) in THF (50 ml) was heated at reflux temperature overnight. The reaction was cooled to room temperature and phosgene (200 ml, 20% in toluene) was added slowly and stirred for an additional 10 min. The mixture was poured into water and extracted with ethyl acetate (3×50 ml). The combined organic layers were washed with brine, dried over Na2SO4 and evaporated under reduced pressure. The residue was triturated with ethanol and filtered to afford 5-chloro-2-phenyl-7,8,9,10-tetrahydro-1,2,4-triazolo[4,3-c]quinazolin-3-one, m.p. 205°-207° C.
Workup
- customprepared
- temperatureat reflux temperature overnight
- extractionextracted with ethyl acetate (3×50 ml)
- washThe combined organic layers were washed with brine
- dry with materialdried over Na2SO4
- customevaporated under reduced pressure
- customThe residue was triturated with ethanol
- filtrationfiltered
Sources & evidence
- ORD record
- ord-d6ffce20ae644e2a90fca3cf7bc04d2a
- Source dataset
- uspto-grants-1997_10
- Patent number
- US05677309
Reaction notes
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