1,4-Dioxane → HCID 23469718, compound

HRID 128461Notes

Reaction equation

HRID 128461 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([C:13]3[CH:18]=[CH:17][C:16]([N+:19]([O-])=O)=[CH:15][CH:14]=3)[N:11]=[CH:10][N:9]=2)=[CH:4][CH:3]=1.O1CCOCC1.O.O.O.O.O.O.O.O.O.[S-2].[Na+].[Na+]>O>[NH2:19][C:16]1[CH:15]=[CH:14][C:13]([N:12]2[C:8]([C:5]3[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=3)=[N:9][CH:10]=[N:11]2)=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 312751,4-DioxaneHCID 73972Sodium sulfide nonahydrateHCID 5339588HCID 5339588, compound

Product 1

HCID 23469718HCID 23469718, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
90 °C

Procedure

A 5.0 g. portion of 5-(p-fluorophenyl)-1-(p-nitrophenyl)-1H-1,2,4-triazole in 42 ml. of dioxane is added to 9.9 g. of sodium sulfide nonahydrate in 42 ml. of water and the mixture is stirred and heated at reflux (90° C.) for 1.5 hours. The solution is cooled and poured into 300 ml. of ice and water with stirring. The solid is collected by filtration, dried, recrystallized from 30 ml. of acetonitrile, washed with ether and dried giving 2.6 g. of the desired product as tan crystals, mp. 147°-150° C.

Workup

  1. temperatureheated
  2. temperatureThe solution is cooled
  3. additionpoured into 300 ml
  4. filtrationThe solid is collected by filtration
  5. customdried
  6. customrecrystallized from 30 ml
  7. washof acetonitrile, washed with ether
  8. customdried
  9. customgiving 2.6 g

Sources & evidence

ORD record
ord-48c0480f115545e3a675a259dbcbbba8
Source dataset
uspto-grants-1981_03
Patent number
US04259504

Reaction notes

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