4,5-Dihydro-2-thiazolamine → N-(2-thiazolin-2-yl)-p-(2-thenoyl)hydratropamide

HRID 258914Notes

Reaction equation

HRID 258914 reaction equation
[NH2:1][C:2]1[S:3][CH2:4][CH2:5][N:6]=1.[C:7]1([C:12]([C:14]2[CH:24]=[CH:23][C:17]([CH:18]([CH3:22])[C:19](Cl)=[O:20])=[CH:16][CH:15]=2)=[O:13])[S:11][CH:10]=[CH:9][CH:8]=1>O1CCOCC1>[S:3]1[CH2:4][CH2:5][N:6]=[C:2]1[NH:1][C:19](=[O:20])[CH:18]([C:17]1[CH:16]=[CH:15][C:14]([C:12](=[O:13])[C:7]2[S:11][CH:10]=[CH:9][CH:8]=2)=[CH:24][CH:23]=1)[CH3:22]

Participants

4

Reactant 2

HCID 156894,5-Dihydro-2-thiazolamineHCID 11747905p-(2-Thenoyl)hydratropoyl chloride

Product 1

HCID 12232966N-(2-thiazolin-2-yl)-p-(2-thenoyl)hydratropamide

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To a stirred and refluxing solution of 3.06 parts of 2-amino-2-thiazoline in 60 parts of dioxane is added a solution of 4.2 parts of p-(2-thenoyl)hydratropoyl chloride in 45 parts of dioxane. Upon completion, stirring at reflux is continued for 30 minutes. The reaction mixture is cooled, filtered and the filtrate is evaporated. The residue is purified by column-chromatography over silicagel, using a mixture of chloroform and 5% of methanol as eluent. The pure fractions are collected and the eluent is evaporated. The residue is crystallized from ethanol, yielding N-(2-thiazolin-2-yl)-p-(2-thenoyl)hydratropamide; mp. 186.4° C.

Workup

  1. stirringUpon completion, stirring
  2. temperatureat reflux
  3. temperatureThe reaction mixture is cooled
  4. filtrationfiltered
  5. customthe filtrate is evaporated
  6. customThe residue is purified by column-chromatography over silicagel
  7. additiona mixture of chloroform and 5% of methanol as eluent
  8. customThe pure fractions are collected
  9. customthe eluent is evaporated
  10. customThe residue is crystallized from ethanol

Sources & evidence

ORD record
ord-a771d199d67a4b6b89f4b57f2a3e0a1d
Source dataset
uspto-grants-1977_07
Patent number
US04035376

Reaction notes

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