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

HRID 1826207Notes

Reaction equation

HRID 1826207 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N+:10]([O-:12])=[O:11])[CH:5]=[C:6]([F:9])[C:7]=1F.C(N(CC)C(C)C)(C)C.[NH:22]1[CH2:27][CH2:26][S:25][CH2:24][CH2:23]1>C(#N)C>[F:9][C:6]1[CH:5]=[C:4]([N+:10]([O-:12])=[O:11])[CH:3]=[C:2]([F:1])[C:7]=1[N:22]1[CH2:27][CH2:26][S:25][CH2:24][CH2:23]1

Participants

5

Reactant 3

HCID 67164Thiomorpholine2×HCID 81531DiisopropylethylamineHCID 27827931,2,3-Trifluoro-5-nitrobenzene

Product 1

HCID 120965924-(2,6-Difluoro-4-nitrophenyl)thiomorpholine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 3,4,5-trifluoronitrobenzene (5.00 g, 28.24 mmol) in acetonitrile (60 mL) was cooled to 0° C. and treated with N,N-diisopropylethylamine (7.38 mL, 42.35 mmol) followed by thiomorpholine (2.98 mL, 29.65 mmol). The ice bath was removed and the reaction mixture stirred at room temperature under nitrogen for approximately 24 hrs, during which additional thiomorpholine (0.1 eq) was added. The solvent was removed under reduced pressure, and the residue was diluted with ethyl acetate, washed with 1N hydrochloric acid (until the washings were acidic), saturated aqueous sodium bicarbonate and saline, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to give the title compound, mp 104-105° C.

Workup

  1. customThe ice bath was removed
  2. additionwas added
  3. customThe solvent was removed under reduced pressure
  4. additionthe residue was diluted with ethyl acetate
  5. washwashed with 1N hydrochloric acid (until the washings
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-eb19fb3e782e4fad898e975b731bf573
Source dataset
uspto-grants-2006_05
Patent number
US07049443B2

Reaction notes

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