Ethylamine → 2-(4-Chloro-phenyl)-N-ethyl-acetamide

HRID 1866528ノート

反応式

HRID 1866528 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=O)=[CH:4][CH:3]=1.[CH2:12]([NH2:14])[CH3:13].O.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.C(N(CC)CC)C>ClCCl.[OH-].[Na+]>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C:9]([NH:14][CH2:12][CH3:13])=[O:11])=[CH:6][CH:7]=1

参加物

8

反応物 5

HCID 6341EthylamineHCID 8471TriethylamineHCID 15880(4-Chlorophenyl)acetic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrate

生成物 1

HCID 44191372-(4-Chloro-phenyl)-N-ethyl-acetamide収率 37%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 14798Sodium Hydroxide溶媒

実験手順

A mixture of 4-chlorophenyl acetic acid (1 g, 5.88 mmol), ethylamine (2M in tetrahydrofuran, 5.88 mL, 11.76 mmol), 1-hydroxybenzotriazole hydrate (90 mg, 5.88 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (1.13 g, 5.88 mmol), and triethylamine 1.78 g, 17.64 mmol) in dichloromethane (30 mL) was stirred at room temperature for 18 hours. The mixture was then diluted with 1M sodium hydroxide solution (30 mL) and the aqueous layer was extracted with dichloromethane (30 mL). The combined organic solution was washed with 1M hydrochloric acid and brine, dried over magnesium sulfate and concentrated in vacuo. The residue was purified by column chromatography on silica gel, eluting with dichloromethane:methanol, 100:0 to 90:10, to afford the title compound as a colourless solid in 37% yield, 443 mg. 1H NMR (400 MHz, CDCl3) δ: 7.31-7.28 (2H, m), 7.27-7.24 (2H, m), 3.45 (2H, s), 3.18 (2H, m), 1.08 (3H, t) ppm; LRMS APCI m/z 198 [M+H]+

後処理

  1. extractionthe aqueous layer was extracted with dichloromethane (30 mL)
  2. washThe combined organic solution was washed with 1M hydrochloric acid and brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by column chromatography on silica gel
  6. washeluting with dichloromethane

出典と根拠

ORDレコード
ord-51b7a4054aa04d6d86028ebcbd428e36
出典データセット
uspto-grants-2009_12
特許番号
US07629358B2

反応ノート

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