Ethanol → 2-(2-benzyloxyphenyl)-N-methylacetamide

HRID 366153Notes

Reaction equation

HRID 366153 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH2:15][C:16]([OH:18])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O[N:20]1[C:24]2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.CN.C(O)C>ClCCl.CN(C)C=O.C(OCC)(=O)C>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH2:15][C:16]([NH:20][CH3:24])=[O:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

9

Reactant 5

HCID 702EthanolHCID 6329MethylamineHCID 757711-HydroxybenzotriazoleHCID 519916(2-Benzyloxyphenyl)acetic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 105871262-(2-benzyloxyphenyl)-N-methylacetamideYield 64.7%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

2-(2-Benzyloxyphenyl)acetic acid (15.0 g, 62 mmol) was dissolved in dichloromethane (270 ml) and N,N-dimethylformamide (70 ml). 1-Hydroxybenzotriazole (8.37 g, 62 mmol) was added. The solution was cooled to 0° C. N-(3-Dimethylaminopropyl)-N'-ethylcarbodiimide hydrochloride (11.89 g, 62 mmol) was added. The reaction mixture was stirred for 20 min. A 8.0 M solution of methylamine in ethanol (38.8 ml, 310 mmol) was added. The solution was stirred for 16 h, while it was warming up to room temperature. It was diluted with ethyl acetate (500 ml) and washed with a 10% aqueous solution of sodium hydrogen sulfate solution (500 ml). The aqueous phase was extracted with ethyl acetate (2×300 ml). The combined organic layers were washed with a saturated aqueous solution of sodium hydrogen carbonate (400 ml) and dried over magnesium sulfate. The solvent was removed in vacuo. The remaining crystalls were washed with a mixture of ethyl acetate/heptane 1:4 (100 ml). They were dried in vacuo. They were dissolved in ethyl acetate. The solution was washed with a saturated aqueous solution of sodium hydrogen carbonate (2×500 ml) and dried over magnesium sulfate. The solvent was removed in vacuo to give 10.24 g of 2-(2-benzyloxyphenyl)-N-methylacetamide.

Workup

  1. stirringThe solution was stirred for 16 h, while it
  2. temperaturewas warming up to room temperature
  3. washwashed with a 10% aqueous solution of sodium hydrogen sulfate solution (500 ml)
  4. extractionThe aqueous phase was extracted with ethyl acetate (2×300 ml)
  5. washThe combined organic layers were washed with a saturated aqueous solution of sodium hydrogen carbonate (400 ml)
  6. dry with materialdried over magnesium sulfate
  7. customThe solvent was removed in vacuo
  8. washThe remaining crystalls were washed with a mixture of ethyl acetate/heptane 1:4 (100 ml)
  9. customThey were dried in vacuo
  10. dissolutionThey were dissolved in ethyl acetate
  11. washThe solution was washed with a saturated aqueous solution of sodium hydrogen carbonate (2×500 ml)
  12. dry with materialdried over magnesium sulfate
  13. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-6c6a6163055149a99033dfe4a7ac2387
Source dataset
uspto-grants-2000_10
Patent number
US06127354

Reaction notes

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