Trimethyl orthobeznoate → 4,8-Dichloro-1-phenyl-[1,2,4]triazolo[4,3-a]quinoxaline

HRID 1731928Notes

Reaction equation

HRID 1731928 reaction equation
CO[C:3](OC)(OC)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[Cl:14][C:15]1[C:24]([NH:25][NH2:26])=[N:23][C:22]2[C:17](=[CH:18][CH:19]=[C:20]([Cl:27])[CH:21]=2)[N:16]=1>>[Cl:14][C:15]1[C:24]2[N:23]([C:3]([C:4]3[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=3)=[N:26][N:25]=2)[C:22]2[C:17]([N:16]=1)=[CH:18][CH:19]=[C:20]([Cl:27])[CH:21]=2

Participants

3

Reactant 2

HCID 69720Trimethyl orthobeznoateHCID 14733462,6-Dichloro-3-hydrazinylquinoxaline

Product 1

HCID 133857054,8-Dichloro-1-phenyl-[1,2,4]triazolo[4,3-a]quinoxaline

Conditions

Temperature
120 °C

Procedure

In a 250 ml. three-necked reaction flask equipped with mechanical stirrer and reflux condenser, there were placed 50.0 g. (0.274 mole) of trimethyl orthobenzoate that had been preheated to ca. 70° C. Stirring was commenced and 10.0 g (0.0437 mole) of 2,6-dichloro-3-hydrazinoquinoxaline, the product of Preparation L(a), were added thereto. The resulting reaction mixture was then heated at ca. 120° C., with continued stirring, for a period of 24 hours, followed by cooling to room temperature (~20° C.) and stirring overnight for approximately 16 hours to give a yellow slurry. The latter slurry was then filtered, and the recovered solid product was subsequently washed with two-50 ml. portions of ethanol and air-dried to constant weight to ultimately afford 9.8 g. (72%) of crude 4,8-dichloro-1-phenyl-[1,2,4]triazolo[4,3-a]quinoxaline, m.p. 305°-307° C. Mass Spectrum: m/e, 316/314 (P+).

Workup

  1. customthree-necked reaction flask equipped with mechanical stirrer
  2. temperaturereflux condenser
  3. customhad been preheated to ca. 70° C
  4. additionwere added
  5. customThe resulting reaction mixture
  6. temperatureby cooling to room temperature (~20° C.)
  7. stirringstirring overnight for approximately 16 hours
  8. customto give a yellow slurry
  9. filtrationThe latter slurry was then filtered
  10. washthe recovered solid product was subsequently washed with two-50 ml
  11. dry with materialportions of ethanol and air-dried to constant weight to ultimately afford 9.8 g

Sources & evidence

ORD record
ord-63ac5e5120c247a4bdf1eff2245e8276
Source dataset
uspto-grants-1986_11
Patent number
US04623725

Reaction notes

Loading…