Ammonia → p-(2-Thenoyl)hydratropamide

HRID 1439586Notes

Reaction equation

HRID 1439586 reaction equation
[NH3:1].[C:2]1([C:7]([C:9]2[CH:19]=[CH:18][C:12]([CH:13]([CH3:17])[C:14](Cl)=[O:15])=[CH:11][CH:10]=2)=[O:8])[S:6][CH:5]=[CH:4][CH:3]=1>CCOCC>[C:2]1([C:7]([C:9]2[CH:19]=[CH:18][C:12]([CH:13]([CH3:17])[C:14]([NH2:1])=[O:15])=[CH:11][CH:10]=2)=[O:8])[S:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 11747905p-(2-Thenoyl)hydratropoyl chloride

Product 1

HCID 12232958p-(2-Thenoyl)hydratropamide

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Gaseous ammonia is introduced through a solution of 5.8 parts of p-(2-thenoyl)hydratropoyl chloride in 80 parts of ether; the product is precipitated as an oil. The solvent is decanted and the oil is stirred in petroleumether. The solvent is decanted each time. The oily residue is dissolved in 2-propanol and the solvent is evaporated. The residue is dissolved in ether and upon the addition of petroleumether, the product is precipitated. It is filtered off and purified by column-chromatography over silicagel, using a mixture of chloroform, methanol and acetone (8 : 1 : 1 by volume). The pure fractions are collected and the solvent is evaporated. The oily residue is triturated in ether. The solid product is filtered off and dried, yielding p-(2-thenoyl)hydratropamide; mp. 108°-124° C.

Workup

  1. customthe product is precipitated as an oil
  2. customThe solvent is decanted
  3. customThe solvent is decanted each time
  4. dissolutionThe oily residue is dissolved in 2-propanol
  5. customthe solvent is evaporated
  6. dissolutionThe residue is dissolved in ether and upon the addition of petroleumether
  7. customthe product is precipitated
  8. filtrationIt is filtered off
  9. custompurified by column-chromatography over silicagel
  10. additiona mixture of chloroform, methanol and acetone (8 : 1 : 1 by volume)
  11. customThe pure fractions are collected
  12. customthe solvent is evaporated
  13. customThe oily residue is triturated in ether
  14. filtrationThe solid product is filtered off
  15. customdried

Sources & evidence

ORD record
ord-df4b15279c1e4306ad243f6f185473f2
Source dataset
uspto-grants-1977_11
Patent number
US04060528

Reaction notes

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