Thiomorpholine → HCID 2732236, compound

HRID 1042723Notes

Reaction equation

HRID 1042723 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13].[NH:15]1[CH2:20][CH2:19][S:18][CH2:17][CH2:16]1.C(=O)(O)[O-].[Na+]>C1COCC1>[N+:12]([C:3]1[CH:4]=[C:5]([C:8]([F:11])([F:10])[F:9])[CH:6]=[CH:7][C:2]=1[N:15]1[CH2:20][CH2:19][S:18][CH2:17][CH2:16]1)([O-:14])=[O:13]

Participants

5

Reactant 3

HCID 67164ThiomorpholineHCID 677784-Fluoro-3-nitrobenzotrifluorideHCID 516892Sodium Bicarbonate

Product 1

HCID 2732236HCID 2732236, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-fluoro-2-nitro-4-(trifluoromethyl)benzene (7.00 g, 33.48 mmol) in THF (250 ml) at room temperature was added thiomorpholine (3.45 g, 33.48 mmol) and sodium bicarbonate (3.66 g, 43.52 mmol). The vessel was purged with nitrogen and stirred at room temperature for 48 hours. After removal of solvent under reduced pressure, the mixture was taken up in ethyl acetate and filtered. The organics were washed with water, then brine and dried with magnesium sulfate. Filtration and concentration provided the title compound as a bright orange solid. MS m/z: 293.1 (M+H+); calc MW=292.28.

Workup

  1. customThe vessel was purged with nitrogen
  2. customAfter removal of solvent under reduced pressure
  3. filtrationfiltered
  4. washThe organics were washed with water
  5. dry with materialbrine and dried with magnesium sulfate
  6. filtrationFiltration and concentration

Sources & evidence

ORD record
ord-187609a9f35041f096f8603173ee76be
Source dataset
uspto-grants-2013_10
Patent number
US08557996B2

Reaction notes

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