N-bromobutanimide → HCID 44549921, compound

HRID 2238431Notes

Reaction equation

HRID 2238431 reaction equation
[CH3:1][S:2]([C:5]1[CH:14]=[C:13]2[C:8]([CH:9]=[CH:10][C:11]([NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[CH:12]2)=[CH:7][CH:6]=1)(=[O:4])=[O:3].C1C(=O)N([Br:30])C(=O)C1>CC#N>[Br:30][C:12]1[C:13]2[C:8](=[CH:7][CH:6]=[C:5]([S:2]([CH3:1])(=[O:3])=[O:4])[CH:14]=2)[CH:9]=[CH:10][C:11]=1[NH:15][C:16](=[O:22])[O:17][C:18]([CH3:19])([CH3:21])[CH3:20]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 44549666HCID 44549666, compound

Product 1

HCID 44549921HCID 44549921, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 202 (2.05 g, 6.38 mmol) and NBS (1.31 g, 7.36 mmol) in MeCN (40 mL) was stirred at reflux for 2 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/EtOAc (19:1), followed by recrystallization from MeOH to give tert-butyl 1-bromo-7-(methylsulfonyl)-2-naphthylcarbamate (203) (2.37 g, 93%) as a white solid: mp 166-167° C.; 1H NMR [(CD3)2SO] δ 8.99 (s, 1H), 8.70 (d, J=1.7 Hz, 1H), 8.25 (d, J=8.5 Hz, 1H), 8.10 (d, J=8.8 Hz, 1H), 8.00 (dd, J=8.5, 1.8 Hz, 1H), 7.97 (d, J=8.9 Hz, 1H), 3.32 (s, 3H), 1.50 (s, 9H). Anal. (C16H18BrNO4S) C, H, N.

Workup

  1. temperatureat reflux for 2 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/EtOAc (19:1)
  9. customfollowed by recrystallization from MeOH

Sources & evidence

ORD record
ord-361436e66720427d84c9e71486c776f3
Source dataset
uspto-grants-2010_05
Patent number
US07718688B2

Reaction notes

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