Ethyl Acetate → 4-(4-Nitrophenyl)thiomorpholine

HRID 1181950Notes

Reaction equation

HRID 1181950 reaction equation
F[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(OCC)(=O)C.C(=O)(O)[O-].[Na+]>C1(C)C=CC=CC=1>[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

6

Reactant 4

HCID 8857Ethyl AcetateHCID 9590p-FluoronitrobenzeneHCID 67164ThiomorpholineHCID 516892Sodium Bicarbonate

Product 1

HCID 31247254-(4-Nitrophenyl)thiomorpholine

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

4-Fluoronitrobenzene (3.0 g, 21.3 mmol) was dissolved in toluene (25 mL). Thiomorpholine (2.4 mL, 23.4 mmol) was added and the mixture stirred overnight at 100° C. At 17 h, the mixture was distributed between ethyl acetate (100 mL) and saturated sodium bicarbonate (50 mL). The organic layer was separated, dried (Na2SO4), filtered and concentrated under vacuum. The residue was triturated with hexane to yield a bright yellow solid.

Workup

  1. waitAt 17 h
  2. customThe organic layer was separated
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum
  6. customThe residue was triturated with hexane
  7. customto yield a bright yellow solid

Sources & evidence

ORD record
ord-bfb03cd710474b6f8529cffcf9ca4227
Source dataset
uspto-grants-2007_10
Patent number
US07285662B2

Reaction notes

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