Ethanol → 1-(Ethoxycarbonyl)ethyl 4-(hexadecylamino)-benzoate

HRID 126937Notes

Reaction equation

HRID 126937 reaction equation
[CH2:1]([NH:17][C:18]1[CH:26]=[CH:25][C:21]([C:22]([O-:24])=[O:23])=[CH:20][CH:19]=1)[CH2:2][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][CH3:16].[Na+].C(O)C.S(O[CH:42]([CH3:48])[C:43]([O:45][CH2:46][CH3:47])=[O:44])(C1C=CC(C)=CC=1)(=O)=O>O>[CH2:1]([NH:17][C:18]1[CH:19]=[CH:20][C:21]([C:22]([O:24][CH:42]([C:43]([O:45][CH2:46][CH3:47])=[O:44])[CH3:48])=[O:23])=[CH:25][CH:26]=1)[CH2:2][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][CH3:16]

Participants

5

Reactant 3

HCID 702EthanolHCID 562846Ethyl 2-[(4-methylbenzenesulfonyl)oxy]propanoateHCID 23703815Cetaben Sodium

Product 1

HCID 234577911-(Ethoxycarbonyl)ethyl 4-(hexadecylamino)-benzoate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a warm mixture of 7 g. (18.3 m moles) sodium 4-(hexadecylamino)benzoate in 100 ml. ethanol is added 4.7 g. (18.3 m moles) 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-fba1507b095a4d08a6a45189a123f12d
Source dataset
uspto-grants-1981_03
Patent number
US04254138

Reaction notes

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