Thiomorpholine → 4-(2,6-Difluoro-4-nitrophenyl)thiomorpholine

HRID 1270335Notes

Reaction equation

HRID 1270335 reaction equation
[NH:1]1[CH2:6][CH2:5][S:4][CH2:3][CH2:2]1.[F:7][C:8]1[CH:9]=[C:10]([N+:16]([O-:18])=[O:17])[CH:11]=[C:12]([F:15])[C:13]=1F>C(#N)C>[F:7][C:8]1[CH:9]=[C:10]([N+:16]([O-:18])=[O:17])[CH:11]=[C:12]([F:15])[C:13]=1[N:1]1[CH2:6][CH2:5][S:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 67164ThiomorpholineHCID 27827931,2,3-Trifluoro-5-nitrobenzene

Product 1

HCID 120965924-(2,6-Difluoro-4-nitrophenyl)thiomorpholineYield 88.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Thiomorpholine (728 mg, 7.06 mmol) was added to a stirring solution of 3,4,5-trifluoronitro benzene (500 mg, 2.82 mmol) in acetonitrile (15 mL) and the reaction mixture was refluxed for 5 h. Evaporation of the solvent in a rotavapor under reduced pressure left a pasty mass which was dissolved in ethyl acetate (50 mL). Ethyl acetate portion was washed with water (30 mL×2) followed by brine (30 mL) and dried over sodium sulfate. Removal of volatiles yielded the title compound as yellow solid (650 mg, 85%).

Workup

  1. temperaturethe reaction mixture was refluxed for 5 h
  2. customEvaporation of the solvent in a rotavapor under reduced pressure
  3. waitleft a pasty mass which
  4. dissolutionwas dissolved in ethyl acetate (50 mL)
  5. washEthyl acetate portion was washed with water (30 mL×2)
  6. dry with materialdried over sodium sulfate
  7. customRemoval of volatiles

Sources & evidence

ORD record
ord-ca29d2c34cfa44b985adb5a9b3585138
Source dataset
uspto-grants-2007_04
Patent number
US07202254B2

Reaction notes

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