Ethanolamine → N-(2-hydroxyethyl)-p-(2-thenoyl)hydratropamide

HRID 461746Notes

Reaction equation

HRID 461746 reaction equation
[NH2:1][CH2:2][CH2:3][OH:4].[C:5]1([C:10]([C:12]2[CH:22]=[CH:21][C:15]([CH:16]([CH3:20])[C:17](Cl)=[O:18])=[CH:14][CH:13]=2)=[O:11])[S:9][CH:8]=[CH:7][CH:6]=1>C(Cl)(Cl)Cl>[OH:4][CH2:3][CH2:2][NH:1][C:17](=[O:18])[CH:16]([C:15]1[CH:14]=[CH:13][C:12]([C:10](=[O:11])[C:5]2[S:9][CH:8]=[CH:7][CH:6]=2)=[CH:22][CH:21]=1)[CH3:20]

Participants

4

Reactant 2

HCID 700EthanolamineHCID 11747905p-(2-Thenoyl)hydratropoyl chloride

Product 1

HCID 12232965N-(2-hydroxyethyl)-p-(2-thenoyl)hydratropamide

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a stirred solution of 2.44 parts of 2-aminoethanol in 15 parts of chloroform is added dropwise a solution of 5.6 parts of p-(2-thenoyl)hydratropoyl chloride in 15 parts of chloroform at room temperature (highly exothermic reaction). Upon completion, the whole is stirred and refluxed for 1 hour. The reaction mixture is cooled and washed with a 1N hydrochloric acid solution. The organic layer is separated, washed twice with water, dried, filtered and evaporated. The oily residue solidifies on triturating in petroleumether. The solid product is filtered off and crystallized from boiling ether, yielding N-(2-hydroxyethyl)-p-(2-thenoyl)hydratropamide; m.p. 87.1° C.

Workup

  1. customhighly exothermic reaction)
  2. temperaturerefluxed for 1 hour
  3. temperatureThe reaction mixture is cooled
  4. washwashed with a 1N hydrochloric acid solution
  5. customThe organic layer is separated
  6. washwashed twice with water
  7. customdried
  8. filtrationfiltered
  9. customevaporated
  10. customon triturating in petroleumether
  11. filtrationThe solid product is filtered off
  12. customcrystallized

Sources & evidence

ORD record
ord-a9e41c60a2a04d6d817f6887c40a5bea
Source dataset
uspto-grants-1977_12
Patent number
US04064132

Reaction notes

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