N-bromobutanimide → HCID 44549796, compound

HRID 2238406Notes

Reaction equation

HRID 2238406 reaction equation
[CH3:1][S:2]([C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[CH:11]=[C:10]([NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])[CH:9]=[CH:8]2)(=[O:4])=[O:3].C1C(=O)N([Br:30])C(=O)C1>CC#N>[Br:30][C:11]1[C:12]2[C:7](=[CH:6][C:5]([S:2]([CH3:1])(=[O:3])=[O:4])=[CH:14][CH:13]=2)[CH:8]=[CH:9][C:10]=1[NH:15][C:16](=[O:22])[O:17][C:18]([CH3:19])([CH3:21])[CH3:20]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 44549528HCID 44549528, compound

Product 1

HCID 44549796HCID 44549796, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 161 (4.47 g, 13.91 mmol) and NBS (2.72 g, 1528 mmol) in MeCN (80 mL) was stirred at reflux for 3 h, then concentrated under reduced pressure. The residue was dissolved in CH2Cl2 and the solution was washed with 10% aqueous Na2SO3 and water, dried, and concentrated under reduced pressure. The residue was purified by chromatography on silica gel, eluting with CH2Cl2, to give tert-butyl 1-bromo-6-(methylsulfonyl)-2-naphthylcarbamate (162) (4.79 g, 86%) as a white solid: mp (MeOH) 190° C.; 1H NMR [(CD3)2SO] δ 8.95 (s, 1H), 8.61 (d, J=1.8 Hz, 1H), 8.36 (d, J=9.0 Hz, 1H), 8.22 (d, J=8.8 Hz, 1H), 8.08 (dd, J=9.0, 1.9 Hz, 1H), 7.96 (d, J=8.9 Hz, 1H), 3.25 (after D2O exchange, s, 3H), 1.50 (s, 9H). Anal. (C16H18BrNO4S) C, H, N.

Workup

  1. temperatureat reflux for 3 h
  2. concentrationconcentrated under reduced pressure
  3. dissolutionThe residue was dissolved in CH2Cl2
  4. washthe solution was washed with 10% aqueous Na2SO3 and water
  5. customdried
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by chromatography on silica gel
  8. washeluting with CH2Cl2

Sources & evidence

ORD record
ord-06a1d00ccf244deb89aba2a42394a628
Source dataset
uspto-grants-2010_05
Patent number
US07718688B2

Reaction notes

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