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

HRID 395258Notes

Reaction equation

HRID 395258 reaction equation
FC(F)(F)S(O[C:7]1[C:12]([F:13])=[CH:11][C:10]([N+:14]([O-:16])=[O:15])=[CH:9][C:8]=1[F:17])(=O)=O.[NH:20]1[CH2:25][CH2:24][S:23][CH2:22][CH2:21]1>O1CCCC1>[F:13][C:12]1[CH:11]=[C:10]([N+:14]([O-:16])=[O:15])[CH:9]=[C:8]([F:17])[C:7]=1[N:20]1[CH2:25][CH2:24][S:23][CH2:22][CH2:21]1

Participants

4

Reactant 2

HCID 67164ThiomorpholineHCID 181734322,6-Difluoro-4-nitrophenyl trifluoromethanesulfonate

Product 1

HCID 120965924-(2,6-Difluoro-4-nitrophenyl)thiomorpholineYield 64%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

2,6-Difluoro-4-nitrophenyl trifluoromethanesulfonate (992 mg, 3.23 mmol) is dissolved in dry tetrahydrofuran (15 mL) and then treated dropwise with thiomorpholine (0.487 mL, 4.85 mmol). The reaction is then heated to reflux (70° C.) under nitrogen for 16 hours. The reaction is then allowed to cool to room temperature, stirring over the weekend (56 hours) under nitrogen. At this time, the reaction is found to be complete by thin layer chromatography. The reaction mixture is concentrated under reduced pressure to yield a yellow solid and then absorbed onto silica gel (25 g). The material is then chromatographed on more silica gel (75 g, packed with hexane), eluting with 5% ethyl acetate/hexane to give 535 mg (64%) of the title compound as a solid, mp: 104-105° C.

Workup

  1. temperatureThe reaction is then heated
  2. temperatureto cool to room temperature
  3. concentrationThe reaction mixture is concentrated under reduced pressure
  4. customto yield a yellow solid
  5. customabsorbed onto silica gel (25 g)
  6. customThe material is then chromatographed on more silica gel (75 g, packed with hexane)
  7. washeluting with 5% ethyl acetate/hexane

Sources & evidence

ORD record
ord-79b20044058b4eb2b38bd4275049cb9f
Source dataset
uspto-grants-2003_08
Patent number
US06605609B2

Reaction notes

Loading…