Ethyl Acetate → 4-(4-Nitrophenyl)thiomorpholine

HRID 2414491Notes

Reaction equation

HRID 2414491 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-1a50c95936d4455cbe0c00f8971d7165
Source dataset
uspto-grants-2004_11
Patent number
US06812225B2

Reaction notes

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