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

HRID 2058758Notes

Reaction equation

HRID 2058758 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. 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-77c1dfe774d34a649ddb6c4f5e4ec8dd
Source dataset
uspto-grants-1982_03
Patent number
US04318914

Reaction notes

Loading…