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

HRID 450046Notes

Reaction equation

HRID 450046 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 71%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A mixture of 1-chloro-4-nitro benzene (1.5 g, 9.5 mmol) and thiomorpholine (1.0 g, 9.7 mmol) was refluxed in n-butanol overnight. The solvent was evaporated under reduced pressure to give a residue, which on triturating with water gave a precipitate. The solid was filtered and washed thoroughly with water, followed by a small amount of pet ether to yield crude solid. Recrystallisation with ethanol yielded 4-(4-nitro-phenyl)-thiomorpholine (1.5 g, 71%).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. customto give a residue, which
  3. customon triturating with water
  4. customgave a precipitate
  5. filtrationThe solid was filtered
  6. washwashed thoroughly with water
  7. customto yield crude solid
  8. customRecrystallisation with ethanol

Sources & evidence

ORD record
ord-ea94191907f048daa0ac4a31155b6343
Source dataset
uspto-grants-2013_07
Patent number
US08486962B2

Reaction notes

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