N-bromobutanimide → 4-(4-Amino-3-bromo-phenyl)-1,1-dioxo-hexahydro-1lambda6-thiopyran-4-carbonitrile

HRID 536971ノート

反応式

HRID 536971 の反応式
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:16]#[N:17])[CH2:13][CH2:12][S:11](=[O:15])(=[O:14])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.C1C(=O)N([Br:25])C(=O)C1>C(Cl)Cl>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:16]#[N:17])[CH2:13][CH2:12][S:11](=[O:15])(=[O:14])[CH2:10][CH2:9]2)=[CH:4][C:3]=1[Br:25]

参加物

4

反応物 2

HCID 67184N-bromobutanimideHCID 589950344-(4-Amino-phenyl)-1,1-dioxo-hexahydro-1lambda6-thiopyran-4-carbonitrile

生成物 1

HCID 589950244-(4-Amino-3-bromo-phenyl)-1,1-dioxo-hexahydro-1lambda6-thiopyran-4-carbonitrile収率 90%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

反応条件

温度
0 °C

実験手順

A solution of 4-(4-amino-phenyl)-1,1-dioxo-hexahydro-1λ6-thiopyran-4-carbonitrile (114 mg, 0.455 mmol, as prepared in the previous step) in CH2Cl2 (15 mL) was cooled to 0° C., treated with solid NBS (77.0 mg, 0.433 mmol), and stirred at that temperature for 30 min. The mixture was diluted with CH2Cl2 (20 mL) and washed with satd aq NaHCO3 (1×20 mL). The aqueous layer was extracted with CH2Cl2 (1×20 mL). The combined organic layers were dried over MgSO4 and concentrated in vacuo. Silica gel chromatography of the residue on a 50-g Varian MegaBond Elut SPE column with 50% EtOAc-hexane afforded the title compound (136 mg, 90%) as a white solid. 1H-NMR (CDCl3; 400 MHz): δ 7.53 (d, 1H, J=2.0 Hz), 7.23 (dd, 1H, J=8.4, 2.0 Hz), 6.79 (d, 1H, J=8.0 Hz), 4.40-4.15 (br s, 2H), 3.60-3.45 (m, 2H), 3.26-3.11 (m, 2H), 2.78-2.63 (m, 2H), 2.51-2.38 (m, 2H).

後処理

  1. washwashed with satd aq NaHCO3 (1×20 mL)
  2. extractionThe aqueous layer was extracted with CH2Cl2 (1×20 mL)
  3. dry with materialThe combined organic layers were dried over MgSO4
  4. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-d7ced052386146a2a56557eebdf4c9ed
出典データセット
uspto-grants-2014_10
特許番号
US08859602B2

反応ノート

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