N-bromobutanimide → HCID 59807115, compound

HRID 1922452Notes

Reaction equation

HRID 1922452 reaction equation
[N:1]1([CH:10]2[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11]2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.C1C(=O)N([Br:29])C(=O)C1>CN(C=O)C.O>[Br:29][C:6]1[CH:5]=[C:4]2[C:9](=[CH:8][CH:7]=1)[N:1]([CH:10]1[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11]1)[CH2:2][CH2:3]2

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 59807152HCID 59807152, compound

Product 1

HCID 59807115HCID 59807115, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

A solution of compound 2 (4.15 g, 14.390 mmol) in dry DMF (30 mL) was treated with NBS (2.56 g, 14.390 mmol) in dry DMF (20 mL) at 0° C. and resulting solution was stirred at same temperature for 3 h. The reaction was diluted with water (150 mL) and product was extracted into ethyl acetate (3×30 mL). The combined ethyl acetate layer was washed with water (2×25 mL), brine (25 mL) and dried (Na2SO4). Solvent was evaporated and crude was purified by column chromatography (ethyl acetate:hexanes, 1:4) to obtain compound 3 (5.12 g, 97%) as a syrup. 1H NMR (CDCl3) δ 7.18-7.07 (m, 2H), 6.33 (d, 1H, J=8.7 Hz), 4.13-3.99 (m, 1H), 3.68-3.26 (m, 6H), 2.94 (t, 2H, J=8.1 Hz), 2.17-1.99 (m, 2H), 1.46 (s, 9H); ESI-MS (m/z, %): 390 (MNa+, 6), 368 (MH+, 3), 313, 311(100).

Workup

  1. customresulting solution
  2. extractionwas extracted into ethyl acetate (3×30 mL)
  3. washThe combined ethyl acetate layer was washed with water (2×25 mL), brine (25 mL)
  4. dry with materialdried (Na2SO4)
  5. customSolvent was evaporated
  6. customcrude was purified by column chromatography (ethyl acetate:hexanes, 1:4)

Sources & evidence

ORD record
ord-0180f69633df45858e622898e6ccb304
Source dataset
uspto-grants-2012_05
Patent number
US08173813B2

Reaction notes

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