Water → HCID 15428837, compound

HRID 1489030Notes

Reaction equation

HRID 1489030 reaction equation
[Cl:1][C:2]1[N:11]=[C:10]([NH:12][NH:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.C(N(CC)C(C)C)(C)C.[C:29](Cl)(Cl)=[O:30].O>C1COCC1>[Cl:1][C:2]1[N:11]2[C:29](=[O:30])[N:13]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[N:12]=[C:10]2[C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[N:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6371PhosgeneHCID 81531DiisopropylethylamineHCID 154288362-Chloro-4-phenylhydrazinoquinazoline

Product 1

HCID 15428837HCID 15428837, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 2-chloro-4-phenylhydrazinoquinazoline (2 g, 7.4 mmol) and N,N-diisopropylethylamine (2 ml, 11.4 mmol) in THF was added phosgene (6 ml, 20% in Toluene) slowly, then stirred for additional 5 min. The reaction mixture was poured into water and extracted with ethyl acetate (2×100 ml). The combined organic layers were washed with brine and dried over Na2SO4 and evaporated under reduced pressure. The residue was triturated with ethanol and filtered to afford 5-chloro-2-phenyl-1,2,4-triazolo[4,3-c]quinazolin-3-one (1.8 g) as a yellow solid. m.p. 167°-168° C.

Workup

  1. extractionextracted with ethyl acetate (2×100 ml)
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over Na2SO4
  4. customevaporated under reduced pressure
  5. customThe residue was triturated with ethanol
  6. filtrationfiltered

Sources & evidence

ORD record
ord-ab3233eb6dd74e74b9fe14341621ecb7
Source dataset
uspto-grants-1997_10
Patent number
US05677309

Reaction notes

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