Ethanol → 1-(Ethoxycarbonyl)ethyl 4-[15-(trifluoromethyl)pentadecylamino]benzoate

HRID 1105902Notes

Reaction equation

HRID 1105902 reaction equation
[F:1][C:2]([F:29])([F:28])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][NH:18][C:19]1[CH:27]=[CH:26][C:22]([C:23]([O-:25])=[O:24])=[CH:21][CH:20]=1.[Na+].C(O)C.S(O[CH:45]([CH3:51])[C:46]([O:48][CH2:49][CH3:50])=[O:47])(C1C=CC(C)=CC=1)(=O)=O>O>[F:1][C:2]([F:28])([F:29])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][NH:18][C:19]1[CH:27]=[CH:26][C:22]([C:23]([O:25][CH:45]([C:46]([O:48][CH2:49][CH3:50])=[O:47])[CH3:51])=[O:24])=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 562846Ethyl 2-[(4-methylbenzenesulfonyl)oxy]propanoateHCID 23671968Sodium 4-[15-(trifluoromethyl)pentadecylamino]benzoate

Product 1

HCID 205494081-(Ethoxycarbonyl)ethyl 4-[15-(trifluoromethyl)pentadecylamino]benzoate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a warm mixture of 7 g. sodium 4-[15-(trifluoromethyl)pentadecylamino]benzoate in 100 ml. ethanol is added 4.7 g. of ethyl α-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 the product 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-3f00ea5af00644c089e957a81b298366
Source dataset
uspto-grants-1982_01
Patent number
US04310545

Reaction notes

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