Triethylamine → HCID 52679100, compound

HRID 1500266Notes

Reaction equation

HRID 1500266 reaction equation
F[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9].C(N(CC)CC)C.[NH:18]1[CH2:23][CH2:22][S:21][CH2:20][CH2:19]1>O1CCOCC1>[N+:8]([C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[N:18]1[CH2:23][CH2:22][S:21][CH2:20][CH2:19]1)([O-:10])=[O:9]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 67164ThiomorpholineHCID 738951-Fluoro-2-nitrobenzene

Product 1

HCID 52679100HCID 52679100, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of 1-fluoro-2-nitro-benzene (2.0 mmol, 0.21 mL), triethylamine (3.0 mmol, 0.42 mL) and thiomorpholine (3.0 mmol, 0.30 mL) in dioxane (2 mL) was irradiated using microwave for 15 minutes at a temperature of 160° C. The solution was then cooled to room temperature and concentrated in vacuo and the resulting residue was purified using column chromatography on silica gel to provide 4-(2-Nitro-phenyl)-thiomorpholine. To the solution of this nitro compound in MeOH (10 mL) was added Pd on carbon (5% Pd, 100 mg). The resulting reaction mixture was stirred under a hydrogen atmosphere at room temperature for about 15 hours. The reaction mixture was filtered through a pad of celite and the filtrate was concentrated in vacuo to provide compound 39A. HPLC-MS RT=1.06 minutes, mass calculated formula C10H14N2S 194.09, observed LCMS m/z 195.10 (M+H).

Workup

  1. customfor 15 minutes
  2. customat a temperature of 160° C
  3. concentrationconcentrated in vacuo
  4. customthe resulting residue was purified

Sources & evidence

ORD record
ord-d04aae778d14486f859946b2a8a7e2b6
Source dataset
uspto-grants-2015_12
Patent number
US09206142B2

Reaction notes

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