Ethanol → 1-(Ethoxycarbonyl)ethyl 4-(allylamino)phenylacetate

HRID 1278312Notes

Reaction equation

HRID 1278312 reaction equation
[CH2:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][C:12]([O-:14])=[O:13])=[CH:7][CH:6]=1)[CH:2]=[CH2:3].[Na+].C(O)C.S(O[CH:30]([CH3:36])[C:31]([O:33][CH2:34][CH3:35])=[O:32])(C1C=CC(C)=CC=1)(=O)=O>O>[CH2:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][C:12]([O:14][CH:30]([C:31]([O:33][CH2:34][CH3:35])=[O:32])[CH3:36])=[O:13])=[CH:7][CH:6]=1)[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 702EthanolHCID 562846Ethyl 2-[(4-methylbenzenesulfonyl)oxy]propanoateHCID 23720721Sodium 4-(allylamino)phenylacetate

Product 1

HCID 211634871-(Ethoxycarbonyl)ethyl 4-(allylamino)phenylacetate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a warm mixture of 7 g. sodium 4-(allylamino)phenylacetate in 100 ml. ethanol is added 4.7 g. ethyl 2-tosyloxypropionate. After 17 hours at reflux, the cooled solution is diluted with an equal volume of water and the resultant precipitate is filtered. After washing with cold ethanol and drying, the product is crystallized from acetonitrile to yield 1-(ethoxycarbonyl)ethyl 4-(allylamino)phenylacetate as colorless crystals.

Workup

  1. additionTo a warm mixture of 7 g
  2. temperatureAfter 17 hours at reflux
  3. filtrationthe resultant precipitate is filtered
  4. washAfter washing with cold ethanol
  5. customdrying
  6. customthe product is crystallized from acetonitrile

Sources & evidence

ORD record
ord-bcb0e3fec60c4029b9726906323c9546
Source dataset
uspto-grants-1981_07
Patent number
US04281019

Reaction notes

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