4-(4-Nitrophenyl)thiomorpholine → 4-Thiomorpholinoaniline

HRID 235620Notes

Reaction equation

HRID 235620 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:15][CH2:14][S:13][CH2:12][CH2:11]2)=[CH:6][CH:5]=1)([O-])=O.[H][H]>O1CCOCC1.[Ni]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([N:10]2[CH2:15][CH2:14][S:13][CH2:12][CH2:11]2)=[CH:8][CH:9]=1

Participants

5

Reactant 2

HCID 31247254-(4-Nitrophenyl)thiomorpholineHCID 178418361HCID 178418361, compound

Product 1

HCID 107742064-Thiomorpholinoaniline

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 312751,4-DioxaneSolvent

Procedure

A solution of 23.47 g of 4-(p-nitrophenyl)-tetrahydro-4H-1,4-thiazine in 1.5 l of dioxane is hydrogenated over Raney-nickel until the hydrogen uptake has finished. Thereafter, the catalyst is removed by filtration, washed well with dioxane and the filtrate is evaporated in vacuo. By recrystallization of the crude product from dichloromethane/ether, there is obtained 4-(p-aminophenyl)-tetrahydro-4H-1,4-thiazine of melting point 109°-111°.

Workup

  1. customThereafter, the catalyst is removed by filtration
  2. washwashed well with dioxane
  3. customthe filtrate is evaporated in vacuo
  4. customBy recrystallization of the crude product from dichloromethane/ether

Sources & evidence

ORD record
ord-da050e0f4637429f847234a784ccecf3
Source dataset
uspto-grants-1987_02
Patent number
US04640918

Reaction notes

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