N-bromobutanimide → Tert-butyl 1-bromo-6-cyano-2-naphthylcarbamate

HRID 2238393

反応式

HRID 2238393 の反応式
[C:1]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])[CH:7]=[CH:6]2)#[N:2].C1C(=O)N([Br:28])C(=O)C1>CC#N>[Br:28][C:9]1[C:10]2[C:5](=[CH:4][C:3]([C:1]#[N:2])=[CH:12][CH:11]=2)[CH:6]=[CH:7][C:8]=1[NH:13][C:14](=[O:20])[O:15][C:16]([CH3:17])([CH3:19])[CH3:18]

参加物

4

反応物 2

HCID 67184N-bromobutanimideHCID 44549529Tert-butyl 6-cyano-2-naphthylcarbamate

生成物 1

HCID 44549797Tert-butyl 1-bromo-6-cyano-2-naphthylcarbamate収率 91%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

A solution of 140 (4.48 g, 18 mmol) and NBS (3.85 g, 21.6 mmol) in MeCN (80 mL) was stirred at reflux for 1 h, then concentrated under reduced pressure. The residue was dissolved in CH2Cl2, washed with 10% aqueous Na2SO3, 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-cyano-2-naphthylcarbamate (141) (5.69 g, 91%): mp (iPr2O/hexane) 164-166° C.; 1H NMR [(CD3)2SO] δ 9.01 (s, 1H), 8.63 (d, J=1.5 Hz, 1H), 8.27 (d, J=9.0 Hz, 1H), 8.07 (d, J=9.0 Hz, 1H), 7.94 (d, J=8.9 Hz, 1H), 7.93 (dd, J=8.9, 1.8 Hz, 1H), 1.50 (s, 9H). Anal. (C16H15BrN2O2) C, H, N, Br.

後処理

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

出典と根拠

ORDレコード
ord-12d9edc40d124302aacf6517a7cc2406
出典データセット
uspto-grants-2010_05
特許番号
US07718688B2

関連ノート

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