Réaction #4856

ord-0f00b2a48ac44f1f81b28c45b15724f2

Équation de réaction

Nc1c(CCO)cc([N+](=O)[O-])cc1[N+](=O)[O-]
2-(2-amino-3,5-dinitrophenyl)ethanol
O.O.O.O.O.O.O.O.O.[Na+].[Na+].[S-2]
sodium sulphide nonahydrate
[S]
sulphur
→
Nc1cc([N+](=O)[O-])cc(CCO)c1N
expected product
Nc1cc([N+](=O)[O-])cc(CCO)c1N
2-(2,3-diamino-5-nitrophenyl)ethanol

Réactifs

Nc1c(CCO)cc([N+](=O)[O-])cc1[N+](=O)[O-]
2-(2-amino-3,5-dinitrophenyl)ethanol
O.O.O.O.O.O.O.O.O.[Na+].[Na+].[S-2]
sodium sulphide nonahydrate
[S]
sulphur

Réactifs

Aucun

Solvants

CC(C)O
isopropanol
O
water
O
water

Conditions de réaction

Conditions détaillées
See reaction.notes.procedure_details.

Traitement

  1. 1
    workup.ADDITIONhas been added
  2. 2
    TempératureHeating
  3. 3
    Températureis maintained for 20 minutes
  4. 4
    workup.ADDITIONafter the addition
  5. 5
    TempératureWhen the mixture is cooled

Mode opératoire

To a suspension of 0.119 mole (27 g) of 2-(2-amino-3,5-dinitrophenyl)ethanol obtained in Example 1 in 67.5 ml of isopropanol to which an equal volume of water has been added, a solutionof 38.4 g of sodium sulphide nonahydrate and 5.4 g of sulphur in 10 ml of water is added dropwise at 60°-65° C. Heating is maintained for 20 minutes after the addition is complete. When the mixture is cooled, a precipitate of the expected product is obtained, and this is drained, made into a paste in water and then recrystallized from 96° strength alcohol. It melts at 172° C.

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US04727192uspto-grants-1988_02