Benzene, (triethoxymethyl)- → 4-Chloro-1-phenyl-[1,2,4]triazolo[4,3-a]quinoxaline

HRID 464303

Reaction equation

HRID 464303 reaction equation
[Cl:1][C:2]1[C:11]([NH:12][NH2:13])=[N:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.CCO[C:17](OCC)(OCC)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C(O)C>[Cl:1][C:2]1[C:11]2[N:10]([C:17]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[N:13][N:12]=2)[C:9]2[C:4]([N:3]=1)=[CH:5][CH:6]=[CH:7][CH:8]=2

Participants

4

Reactant 2

HCID 74268Benzene, (triethoxymethyl)-HCID 36588202-Chloro-3-hydrazinoquinoxaline

Product 1

HCID 8992904-Chloro-1-phenyl-[1,2,4]triazolo[4,3-a]quinoxaline

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-Chloro-3-hydrazinoquinoxaline (2.2 g., 0.011 mole) was mixed with 6 ml. of triethyl orthobenzoate and heated at 100° C. for 30 minutes. After cooling the orange mixture to room temperature, ethanol was added. Filtration of the resultant precipitate afforded 2.1 g. of crude product which was further purified by means of trituration with warm methanol, followed by filtration and air drying to ultimately yield 1.58 g. (51%) of pure 4-chloro-1-phenyl-[1,2,4]triazolo[4,3-a]quinoxaline as an orange solid.

Workup

  1. filtrationFiltration of the resultant precipitate
  2. customafforded 2.1 g
  3. customof crude product which was further purified by means of trituration with warm methanol
  4. filtrationfollowed by filtration and air
  5. customdrying to ultimately yield 1.58 g

Sources & evidence

ORD record
ord-115b1a55758241a79305b5a4ab1f0ffc
Source dataset
uspto-grants-1985_10
Patent number
US04547501

Linked notes

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