Dimethylformamide → HCID 18617606、化合物

HRID 1264203ノート

反応式

HRID 1264203 の反応式
P(Cl)(Cl)([Cl:3])=O.O[CH2:7][CH2:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][CH:13]=[CH:12]2.CN([CH:21]=[O:22])C>>[Cl:3][CH2:7][CH2:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][CH:13]=[C:12]2[CH:21]=[O:22]

参加物

4

反応物 3

HCID 6228Dimethylformamide2 回HCID 24813Phosphorus oxychlorideHCID 186174542-(5-indolyl)ethanol

生成物 1

HCID 18617606HCID 18617606、化合物収率 90%

反応条件

温度
80 °C

実験手順

A solution of 1.46 mL (15.7 mmol) phosphorous oxychloride in 5 mL DMF is stirred for 20 minutes. A solution of 2.11 g (13.1 mmol) 5-(2-hydroxyethyl)indole (reference example 6) in 5 mL DMF is added, and the reaction mixture is heated to 80° C. for ten minutes. The reaction is quenched with solid sodium bicarbonate and diluted with 250 mL 1:1 CH2Cl2:MeOH. The inorganic solids are filtered off, and the filtrate concentrated. The resulting residue is refluxed in 75 mL 1N HCl solution for one hour, then extracted with CH2Cl2. The organic extracts are combined and concentrated, and the residue chromatographed (20:1 CH2Cl2:MeOH) to provide 2.45 g of the product as a brown solid in 90% yield. 1H NMR (CDCl3): δ 3.19 (2H, t, J=7 Hz), 3.76 (2H, t, J=7 Hz), 7.20 (1H, dd, J=8, 1 Hz), 7.40 (1H, d, J=8 Hz), 7.85 (1H, d, J=3 Hz), 8.19 (1H, s), 8.98 (1H, br), 10.05 (1H, s). MS (EI) m/z 207, 209 (M[35Cl, 37Cl])+, 158 (M−CH2Cl)+.

後処理

  1. customThe reaction is quenched with solid sodium bicarbonate
  2. additiondiluted with 250 mL 1:1 CH2Cl2
  3. filtrationThe inorganic solids are filtered off
  4. concentrationthe filtrate concentrated
  5. temperatureThe resulting residue is refluxed in 75 mL 1N HCl solution for one hour
  6. extractionextracted with CH2Cl2
  7. concentrationconcentrated
  8. customthe residue chromatographed (20:1 CH2Cl2:MeOH)

出典と根拠

ORDレコード
ord-aed3470732e144979fb4a2b68379b1a7
出典データセット
uspto-grants-2003_04
特許番号
US06541505B1

反応ノート

読み込み中…