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

HRID 1866528Notes

Reaction equation

HRID 1866528 reaction equation
[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

Participants

8

Reactant 5

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 14798Sodium HydroxideSolvent

Procedure

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]+

Workup

  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

Sources & evidence

ORD record
ord-51b7a4054aa04d6d86028ebcbd428e36
Source dataset
uspto-grants-2009_12
Patent number
US07629358B2

Reaction notes

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