HCID 13269216, compound → HCID 13269217, compound

HRID 370579Notes

Reaction equation

HRID 370579 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:23]=[CH:24][CH:25]=1)[C:7]([NH:9][CH2:10][CH2:11][S:12][CH2:13][C:14]1[O:15][C:16]([CH2:19][N:20]([CH3:22])[CH3:21])=[CH:17][CH:18]=1)=[O:8])([O-])=O>[Fe]>[NH2:1][C:4]1[CH:5]=[C:6]([CH:23]=[CH:24][CH:25]=1)[C:7]([NH:9][CH2:10][CH2:11][S:12][CH2:13][C:14]1[O:15][C:16]([CH2:19][N:20]([CH3:21])[CH3:22])=[CH:17][CH:18]=1)=[O:8]

Participants

3

Reactant 1

HCID 13269216HCID 13269216, compound

Product 1

HCID 13269217HCID 13269217, compoundYield 75.5%

Reagents, catalysts & solvents 1

HCID 23925IronCatalyst

Procedure

To a suspension of 13 g of 3-nitro-N-[2-(5-dimethylaminomethylfuran-2-ylmethylthio)ethyl]benzamide and 8 g of metallic iron, previously washed with 2N hydrochloric acid, in a mixture of 50 ml of water and 50 ml of methanol, concentrated hydrochloric acid is added dropwise and under stirring until pH 5, then the mixture is heated two hours with reflux. After cooling, the precipitate is filtered and thoroughly washed with methanol. The solution so obtained is evaporated under reduced pressure to eliminate the methanol. The pH of the aqueous solution is adjusted to 10 with sodium hydroxide and the inorganic precipitate which forms is eliminated after washing with ethanol. The solution is extracted 4 times with 40 ml of ethyl acetate containing 10% of ethanol, the solution is dried on anhydrous sodium sulfate and evaporated to dryness. Thus, 9 g of 3-amino-N-[2-(5-dimethylaminomethylfuran-2-ylmethylthio)ethyl]benzamide are obtained as an oil.

Workup

  1. washpreviously washed with 2N hydrochloric acid, in a mixture of 50 ml of water and 50 ml of methanol, concentrated hydrochloric acid
  2. additionis added dropwise
  3. temperaturethe mixture is heated two hours
  4. temperaturewith reflux
  5. temperatureAfter cooling
  6. filtrationthe precipitate is filtered
  7. washthoroughly washed with methanol
  8. customThe solution so obtained
  9. customis evaporated under reduced pressure
  10. washafter washing with ethanol
  11. extractionThe solution is extracted 4 times with 40 ml of ethyl acetate containing 10% of ethanol
  12. dry with materialthe solution is dried on anhydrous sodium sulfate
  13. customevaporated to dryness

Sources & evidence

ORD record
ord-937a28d5413c4d6f8b2c18ca2f8c6b9e
Source dataset
uspto-grants-1985_07
Patent number
US04526995

Reaction notes

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