Morpholine → 4-[2-(4-Nitro-phenyl)-ethanesulfonyl]-morpholine

HRID 1190124Notes

Reaction equation

HRID 1190124 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][S:12]([OH:15])(=[O:14])=O)=[CH:6][CH:5]=1)([O-:3])=[O:2].S(Cl)(Cl)=O.[NH:20]1[CH2:25][CH2:24][O:23][CH2:22][CH2:21]1>O.C([O-])(O)=O.[Na+]>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([CH2:10][CH2:11][S:12]([N:20]2[CH2:25][CH2:24][O:23][CH2:22][CH2:21]2)(=[O:14])=[O:15])=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

6

Reactant 3

HCID 8083MorpholineHCID 24386Thionyl ChlorideHCID 109113994-Nitrobenzeneethanesulfonic Acid

Product 1

HCID 589943904-[2-(4-Nitro-phenyl)-ethanesulfonyl]-morpholineYield 52%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
80 °C

Procedure

A flask was charged with 491 mg (2.12 mmol) of solid 2-(4-nitro-phenyl)-ethanesulfonic acid (as prepared in the previous step), which was treated with 3.10 mL (42.4 mmol) of thionyl chloride and heated to 80° C. for 7 h. The volatile components were removed in vacuo, the residue was taken up in THF (20 mL), and 927 μL (10.6 mmol) of morpholine was added. The mixture was stirred at RT for 16 h, diluted with water (15 mL) and saturated aqueous NaHCO3 (15 mL) and extracted with EtOAc (2×70 mL). The organic layer was dried (MgSO4) and concentrated in vacuo to afford 370 mg (52%) of the title compound as a pale yellow solid: 1H-NMR (CDCl3; 400 MHz): δ 8.20 (d, 2H, J=8.8 Hz), 7.40 (d, 2H, J=8.8 Hz), 3.79-3.73 (m, 4H), 3.31-3.23 (m, 6H), 3.21-3.14 (m, 2H).

Workup

  1. customas prepared in the previous step), which
  2. customThe volatile components were removed in vacuo
  3. extractionextracted with EtOAc (2×70 mL)
  4. dry with materialThe organic layer was dried (MgSO4)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-90c1149ab379401abaeba348a0662cf1
Source dataset
uspto-grants-2014_03
Patent number
US08674100B2

Reaction notes

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