4-Methylmorpholine → Pyridine-2-sulfonic acid allyl-(2-methyl-pent-4enyl)-amide

HRID 1790599

反応式

HRID 1790599 の反応式
[CH2:1]([NH:4][CH2:5][CH:6]([CH3:10])[CH2:7][CH:8]=[CH2:9])[CH:2]=[CH2:3].CN1CCOCC1.[N:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[S:24](Cl)(=[O:26])=[O:25]>C(Cl)Cl>[CH2:1]([N:4]([CH2:5][CH:6]([CH3:10])[CH2:7][CH:8]=[CH2:9])[S:24]([C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][N:18]=1)(=[O:26])=[O:25])[CH:2]=[CH2:3]

参加物

5

反応物 3

HCID 79724-MethylmorpholineHCID 3787675Pyridine-2-sulfonyl ChlorideHCID 11378535Allyl-(2-methyl-pent-4-enyl)-amine

生成物 1

HCID 11565389Pyridine-2-sulfonic acid allyl-(2-methyl-pent-4enyl)-amide収率 60%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

Allyl-(2-methyl-pent-4-enyl)-amine (1.0 g, 7.2 mmol) and NMM (1.7 g, 17.2 mmol) were mixed in 30 ml CH2Cl2. 2-pyridinesulphonyl chloride (1.53 g, 8.6 mmol) was added slowly to the solution while it was cooled in an ice-water bath. After addition, the reaction mixture was stirred at RT overnight. The reaction mixture was washed with 10% NaHCO3 and the brine, then was purified by column chromatography to give the title compound as a colorless oil (1.2 g ,60% yield): MS (M+H+) 281.2; 1H-NMR (400 Hz, CDCl3): d=8.70(d, 1H), 8.0–7.75(m, 2H), 7.5 (m, 1H) 5.80–5.60(m, 2H), 5.15–4.92(m, 4H), 4.00–3.90(m, 2H), 3.20–3.06(m, 2H), 2.15(m, 1H), 1.85(m, 2H), 0.89(d, 3H).

後処理

  1. temperaturewas cooled in an ice-water bath
  2. additionAfter addition
  3. washThe reaction mixture was washed with 10% NaHCO3
  4. customthe brine, then was purified by column chromatography

出典と根拠

ORDレコード
ord-641d6ec4383d4f94a02c686482e313a0
出典データセット
uspto-grants-2006_07
特許番号
US07071184B2

関連ノート

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