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

HRID 258934Notes

Reaction equation

HRID 258934 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 one 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; mp. 87.1° C.

Workup

  1. customhighly exothermic reaction)
  2. temperaturerefluxed for one 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-2e83a897cdc4418b9283c97192ae0bc7
Source dataset
uspto-grants-1977_07
Patent number
US04035376

Reaction notes

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