N-bromobutanimide → HCID 54850283, compound

HRID 1711278Notes

Reaction equation

HRID 1711278 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10]([N:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)(=[O:12])=[O:11])=[CH:6][CH:5]=1)([O-])=O.C1C(=O)N([Br:26])C(=O)C1>CO.C(Cl)Cl.[Pd]>[Br:26][C:5]1[CH:6]=[C:7]([S:10]([N:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)(=[O:12])=[O:11])[CH:8]=[CH:9][C:4]=1[NH2:1]

Participants

6

Reactant 2

HCID 67184N-bromobutanimideHCID 2362694-[(4-nitrophenyl)sulfonyl]morpholine

Product 1

HCID 54850283HCID 54850283, compoundYield 22.3%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 250 mg (0.918 mmol) of 4-(4-nitro-benzenesulfonyl)-morpholine in MeOH (15 mL) was treated with 20 mg of 10% Pd/C (Degussa type E101-NE/W, Aldrich, 50% by weight water) under H2 (1 atm). The mixture was stirred at RT for 1.5 h and filtered through Celite. The filter cake was washed with MeOH, and the filtrate was concentrated in vacuo. The residue was taken up in CH2Cl2 (10 mL), cooled to 0° C., and treated with 124 mg (0.698 mmol) of NBS at that temperature for 25 min. The mixture was diluted with CH2Cl2 (15 mL) and washed with saturated aqueous NaHCO3 (1×10 mL). The organic layer was dried (MgSO4) and concentrated in vacuo. Silica gel chromatography of the residue on a 50-g Varian MegaBond Elut SPE column with 40-50% EtOAc-hexane afforded 50.0 mg (17%) of the title compound as a pale tan solid: Mass spectrum (ESI, m/z): Calcd. for C10H13N2O3SBr, 321.0 (M+H), found 320.9/322.8.

Workup

  1. filtrationfiltered through Celite
  2. washThe filter cake was washed with MeOH
  3. concentrationthe filtrate was concentrated in vacuo
  4. temperaturecooled to 0° C.
  5. washwashed with saturated aqueous NaHCO3 (1×10 mL)
  6. dry with materialThe organic layer was dried (MgSO4)
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-970fdfc3d4a2403289f22fbac5f6551e
Source dataset
uspto-grants-2010_09
Patent number
US07790724B2

Reaction notes

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