Water → HCID 15428840, compound

HRID 1489035Notes

Reaction equation

HRID 1489035 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)CC)C.[C:27](Cl)(Cl)=[S:28].O>C1COCC1>[Cl:1][C:2]1[N:11]2[C:27](=[S:28])[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 8471TriethylamineHCID 10040ThiophosgeneHCID 154288362-Chloro-4-phenylhydrazinoquinazoline

Product 1

HCID 15428840HCID 15428840, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 2-chloro-4-phenylhydrazinoquinazoline (example I) (600 mg, 2.2 mmol) and triethylamine (800 ml, 5.7 mmol) in THF (50 ml) was added thiophosgene (180 ml, 2.3 mmol) slowly and stirred for additional 5 min. The reaction mixture was poured into water and extracted with CH2 Cl2 (3×50 ml). The combined organic layers were dried over Na2SO4 and evaporated under reduced pressure. The residue was triturated with ethanol and the precipitate was filtered to afford 5-chloro-2-phenyl-1,2,4-triazolo[4,3-c]quinazolin-3-thione.

Workup

  1. extractionextracted with CH2 Cl2 (3×50 ml)
  2. dry with materialThe combined organic layers were dried over Na2SO4
  3. customevaporated under reduced pressure
  4. customThe residue was triturated with ethanol
  5. filtrationthe precipitate was filtered

Sources & evidence

ORD record
ord-033cb719ddf94ee8bae3d51c80dd04c1
Source dataset
uspto-grants-1997_10
Patent number
US05677309

Reaction notes

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