Ethanol → HCID 20536501, compound

HRID 1156119Notes

Reaction equation

HRID 1156119 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[NH:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[C:5]([O-:7])=[O:6].[Na+].C(O)C.S(O[CH:43]([CH3:49])[C:44]([O:46][CH2:47][CH3:48])=[O:45])(C1C=CC(C)=CC=1)(=O)=O>O>[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[NH:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[C:5]([O:7][CH:43]([C:44]([O:46][CH2:47][CH3:48])=[O:45])[CH3:49])=[O:6]

Participants

5

Reactant 3

HCID 702EthanolHCID 562846Ethyl 2-[(4-methylbenzenesulfonyl)oxy]propanoateHCID 23709238HCID 23709238, compound

Product 1

HCID 20536501HCID 20536501, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a warm mixture of 7 g sodium 3-fluoro-4-(hexadecylamino)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 1-(ethoxycarbonyl)ethyl 3-fluoro-4-(hexadecylamino)benzoate as colorless crystals.

Workup

  1. temperatureAfter 17 hours at reflux
  2. filtrationthe resultant precipitate is filtered
  3. washAfter washing with cold ethanol
  4. customdrying
  5. customthe product is crystallized from acetonitrile

Sources & evidence

ORD record
ord-a7b8045a907947379fb81e82ec1cdcd3
Source dataset
uspto-grants-1982_06
Patent number
US04333940

Reaction notes

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