O,O-Dipyridin-2-yl carbonothioate → 2-Ethoxy-8-isothiocyanato-1,4-dihydronaphthalene

HRID 1785535

反応式

HRID 1785535 の反応式
[CH2:1]([O:3][C:4]1[CH2:13][C:12]2[C:11]([NH2:14])=[CH:10][CH:9]=[CH:8][C:7]=2[CH2:6][CH:5]=1)[CH3:2].[C:15](=[S:30])(OC1C=CC=CN=1)OC1C=CC=CN=1>ClCCl>[CH2:1]([O:3][C:4]1[CH2:13][C:12]2[C:7]([CH2:6][CH:5]=1)=[CH:8][CH:9]=[CH:10][C:11]=2[N:14]=[C:15]=[S:30])[CH3:2]

参加物

4

反応物 2

HCID 719784O,O-Dipyridin-2-yl carbonothioateHCID 230669967-Ethoxy-5,8-dihydronaphthalen-1-amine

生成物 1

HCID 866096122-Ethoxy-8-isothiocyanato-1,4-dihydronaphthalene

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

A solution of the product of Example 1E (200 mg, 1.06 mmol) in dichloromethane (2.5 mL) was added to a solution of O,O-dipyridin-2-yl thiocarbonate (246 mg, 1.06 mmol) in dichloromethane (5 mL) at room temperature. After stirring at room temperature for 18 hours, the mixture was concentrated, then filtered through silica gel and eluted with 5% ethyl acetate-hexane. Evaporation of the filtrate in vacuo afforded the title compound as a pale pink solid, 225 mg (92%). 1H NMR (DMSO-d6) δ 7.21-7.27 (m, 3H), 4.86 (t, 1H, J=3.6 Hz), 3.81 (q, 2H, J=7.0 Hz), 3.49 (q, 2H, 4.4 Hz), 3.35 (t, 2H, J=5.2 Hz), 1.27 (t, 3H, J=7.0 Hz); MS (DCI+) m/z 232 (M+H).

後処理

  1. concentrationthe mixture was concentrated
  2. filtrationfiltered through silica gel
  3. washeluted with 5% ethyl acetate-hexane
  4. customEvaporation of the filtrate in vacuo

出典と根拠

ORDレコード
ord-5ba29fd898794ebf8e3230da2c8c99f0
出典データセット
uspto-grants-2009_03
特許番号
US07504520B2

関連ノート

読み込み中…