N-bromobutanimide → HCID 67188040, compound

HRID 885995Notes

Reaction equation

HRID 885995 reaction equation
[CH3:1][C:2]1([CH3:24])[NH:7][C:6](=[O:8])[C:5]2[S:9][C:10]([N:12]3[C:17]4[CH:18]=[CH:19][C:20]([O:22][CH3:23])=[CH:21][C:16]=4[O:15][CH2:14][CH2:13]3)=[N:11][C:4]=2[CH2:3]1.[Br:25]N1C(=O)CCC1=O>CC#N.C1COCC1>[Br:25][C:19]1[C:20]([O:22][CH3:23])=[CH:21][C:16]2[O:15][CH2:14][CH2:13][N:12]([C:10]3[S:9][C:5]4[C:6](=[O:8])[NH:7][C:2]([CH3:24])([CH3:1])[CH2:3][C:4]=4[N:11]=3)[C:17]=2[CH:18]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 44577952HCID 44577952, compound

Product 1

HCID 67188040HCID 67188040, compoundYield 100.8%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of Example 489 (0.05 g, 0.145 mmol) in MeCN (1 mL) and THF (1 mL) was added N-bromosuccinimide (0.026 g, 0.145 mmol). The mixture was stirred at r.t. overnight and then concentrated in vacuo. EtOAc (10 mL) and 1% aqueous sodium sulfite (5 mL) were added and the mixture was rapidly stirred for 10 minutes. The aqueous layer was extracted with EtOAc (10 mL) and then DCM (2×10 mL). The EtOAc extracts were concentrated in vacuo and the residue was dissolved in DCM (5 mL). The combined organic fractions were washed with brine (10 mL), dried (MgSO4), filtered and the solvent was evaporated in vacuo to give the title compound (0.062 g, 100%) as a light brown solid. δH (CDCl3) 8.17 (1H, s), 6.52 (1H, s), 5.22 (1H, s), 4.35-4.30 (2H, m), 4.10-4.05 (2H, m), 3.86 (3H, s), 2.88 (2H, s), 1.39 (6H, s). LCMS (ES+) 424.1, 426.0 (M+H)+, RT 3.47 minutes (Method 1).

Workup

  1. concentrationconcentrated in vacuo
  2. additionEtOAc (10 mL) and 1% aqueous sodium sulfite (5 mL) were added
  3. stirringthe mixture was rapidly stirred for 10 minutes
  4. extractionThe aqueous layer was extracted with EtOAc (10 mL)
  5. concentrationThe EtOAc extracts were concentrated in vacuo
  6. dissolutionthe residue was dissolved in DCM (5 mL)
  7. washThe combined organic fractions were washed with brine (10 mL)
  8. dry with materialdried (MgSO4)
  9. filtrationfiltered
  10. customthe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-405b584162444944a94f7c65c1e2c204
Source dataset
uspto-grants-2012_08
Patent number
US08242116B2

Reaction notes

Loading…