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

HRID 650834Notes

Reaction equation

HRID 650834 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.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

8

Reactant 4

HCID 702EthanolHCID 6329MethylamineHCID 757711-HydroxybenzotriazoleHCID 519916(2-Benzyloxyphenyl)acetic acid

Product 1

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

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

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 IC. 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 crystalIs were washed with a mixture of ethyl acetatelheptane 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. additionwas added
  2. stirringThe solution was stirred for 16 h, while it
  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. customThe remaining crystalIs
  9. washwere washed with a mixture of ethyl acetatelheptane 1:4 (100 ml)
  10. customThey were dried in vacuo
  11. dissolutionThey were dissolved in ethyl acetate
  12. washThe solution was washed with a saturated aqueous solution of sodium hydrogen carbonate (2×500 ml)
  13. dry with materialdried over magnesium sulfate
  14. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-f4b66fd4372c46899a701d01345bc3f7
Source dataset
uspto-grants-2001_08
Patent number
US06274584B1

Reaction notes

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