1-Chloro-4-nitrobenzene → 4-(4-Nitrophenyl)thiomorpholine

HRID 1910775Notes

Reaction equation

HRID 1910775 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1.[NH:11]1[CH2:16][CH2:15][S:14][CH2:13][CH2:12]1>C(O)CCC>[N+:8]([C:5]1[CH:6]=[CH:7][C:2]([N:11]2[CH2:16][CH2:15][S:14][CH2:13][CH2:12]2)=[CH:3][CH:4]=1)([O-:10])=[O:9]

Participants

4

Reactant 2

HCID 74741-Chloro-4-nitrobenzeneHCID 67164Thiomorpholine

Product 1

HCID 31247254-(4-Nitrophenyl)thiomorpholineYield 76%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A solution of 1-chloro-4-nitrobenzene (1.5 g, 9.5 mmol) and thiomorpholine (1.0 g, 9.7 mmol) in n-butanol was heated at reflux for 24 h. The solvent was evaporated under reduced pressure to give a residue, which on trituration with water gave a solid. This was filtered off and washed thoroughly with water then with a small amount of petroleum ether. This gave a solid which was recrystallised from ethanol to yield 4-(4-nitro-phenyl)-thiomorpholine (1.6 g, 76%).

Workup

  1. temperatureat reflux for 24 h
  2. customThe solvent was evaporated under reduced pressure
  3. customto give a residue, which on trituration with water
  4. customgave a solid
  5. filtrationThis was filtered off
  6. washwashed thoroughly with water
  7. customThis gave a solid which
  8. customwas recrystallised from ethanol

Sources & evidence

ORD record
ord-ac84cdcf181748c0adfc53365217eb0a
Source dataset
uspto-grants-2013_12
Patent number
US08604029B2

Reaction notes

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