Ethanolamine → N-(2-Hydroxyethyl)heptanamide

HRID 1708392ノート

反応式

HRID 1708392 の反応式
[CH2:1]([CH2:3][NH2:4])[OH:2].C(N(CC)CC)C.[C:12](Cl)(=[O:19])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].O>O1CCCC1>[OH:2][CH2:1][CH2:3][NH:4][C:12](=[O:19])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

参加物

6

反応物 4

HCID 700EthanolamineHCID 962WaterHCID 8471TriethylamineHCID 17313Heptanoyl chloride

生成物 1

HCID 14455153N-(2-Hydroxyethyl)heptanamide

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

A solution of ethanolamine (8.00 mL, 133 mmol) and triethylamine (20.0 mL, 143 mmol) in tetrahydrofuran (200 mL) was cooled to 0° C., and a solution of heptanoyl chloride (20.0 mL, 129 mmol) in tetrahydrofuran (50 mL) was added dropwise over 30 minutes. After stirring an additional 18 hours, the reaction mixture was poured into water (400 mL), and extracted with methylene chloride (2×300 mL). The extracts were combined, dried over anhydrous magnesium sulfate and evaporated to afford the solid product (N-(2-hydroxyethyl)-heptanamide), which was recrystallized to purity from ether-hexane (22.3 g, 129 mmol, 100%), melting point 91°-93° C. 1H NMR (CDCl3): 6.31 (1H, br s); 3.75-3.68 (2H, m); 3.55-3.39 (3H, m); 2.21 (2H, t, J=7.2 Hz); 1.69-1.58 (2H, m); 1.39-1.24 (6H, m); 0.88 (3H, t, J=6.6 Hz).

後処理

  1. extractionextracted with methylene chloride (2×300 mL)
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customevaporated

出典と根拠

ORDレコード
ord-b55d9ba50765499eb7f87c5ed3cff4b7
出典データセット
uspto-grants-1994_10
特許番号
US05358946

反応ノート

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