Ethanol → HCID 20498876, compound

HRID 128336Notes

Reaction equation

HRID 128336 reaction equation
[CH:1]1([CH2:7][CH2:8][NH:9][C:10]2[CH:15]=[CH:14][C:13]([CH2:16][C:17]([O-:19])=[O:18])=[CH:12][CH:11]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[Na+].C(O)C.S(O[CH:35]([CH3:41])[C:36]([O:38][CH2:39][CH3:40])=[O:37])(C1C=CC(C)=CC=1)(=O)=O>O>[CH:1]1([CH2:7][CH2:8][NH:9][C:10]2[CH:15]=[CH:14][C:13]([CH2:16][C:17]([O:19][CH:35]([C:36]([O:38][CH2:39][CH3:40])=[O:37])[CH3:41])=[O:18])=[CH:12][CH:11]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 702EthanolHCID 562846Ethyl 2-[(4-methylbenzenesulfonyl)oxy]propanoateHCID 23717728HCID 23717728, compound

Product 1

HCID 20498876HCID 20498876, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a warm mixture of 7 g. sodium 4-(2-cyclohexylethylamino)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-(2-cyclohexylethylamino)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-90cc2478d06142dda214207fde4a1a19
Source dataset
uspto-grants-1981_03
Patent number
US04259352

Reaction notes

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