Triethylamine → 2-(benzyloxy)-N-(2-chloro-5-methoxyphenyl)acetamide

HRID 628696Notes

Reaction equation

HRID 628696 reaction equation
[CH2:1]([O:8][CH2:9][C:10](Cl)=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[Cl:14][C:15]1[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][C:16]=1[NH2:17].C(N(CC)CC)C>ClCCl>[CH2:1]([O:8][CH2:9][C:10]([NH:17][C:16]1[CH:18]=[C:19]([O:22][CH3:23])[CH:20]=[CH:21][C:15]=1[Cl:14])=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 177085Benzyloxyacetyl chlorideHCID 27239002-Chloro-5-methoxyanilinium chloride

Product 1

HCID 666798212-(benzyloxy)-N-(2-chloro-5-methoxyphenyl)acetamideYield 103%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Benzyloxy acetyl chloride (1) (11.0 g, 60.0 mmol) and 2-chloro-5-methoxyaniline hydrochloride (11.7 g, 60.2 mmol) in dichloromethane (100 mL) at 0° C., was stirred and triethylamine (13.0 g 126.0 mmol, 18.0 mL) added slowly over 15 min. The stirred reaction was allowed to warm to RT over 18 h. There was a heavy precipitation of triethylamine hydrochloride. The dichloromethane solution was washed with 10% aqueous potassium carbonate (50 mL), dried over magnesium sulfate and concentrated in vacuo to afford 18.9 g (quantitative) of 2-Benzyloxy-N-(2-chloro-5-methoxy-phenyl)acetamide (2) as a gum. The structure was confirmed by 13C NMR (75 MHz, CDCl3): δC 55.6, 69.6, 73.6, 106.2, 111.1, 114.1, 127.7, 128.3, 128.6, 129.2, 134.6, 136.5, 158.9, and 167.7.

Workup

  1. customThe stirred reaction
  2. customa heavy precipitation of triethylamine hydrochloride
  3. washThe dichloromethane solution was washed with 10% aqueous potassium carbonate (50 mL)
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ed341c510f504fc6a4e2b02bbe831056
Source dataset
uspto-grants-2016_04
Patent number
US09314541B2

Reaction notes

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