Hydrochloric Acid → HCID 22414500, compound

HRID 1721338Notes

Reaction equation

HRID 1721338 reaction equation
[CH3:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[CH:7]([NH:19][CH3:20])[CH2:8][C:9]1[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][C:10]=1[N+:16]([O-])=O.[ClH:21]>C(O)C.O.[Fe]>[ClH:15].[ClH:21].[NH2:16][C:10]1[CH:11]=[C:12]([Cl:15])[CH:13]=[CH:14][C:9]=1[CH2:8][CH:7]([C:3]1[S:4][CH:5]=[CH:6][C:2]=1[CH3:1])[NH:19][CH3:20]

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 9972719HCID 9972719, compound

Product 1

HCID 22414500HCID 22414500, compound

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of 10 g of α-(3-methyl-2-thienyl)-N-methyl-4-chloro-2-nitrobenzeneethana mine in 150 ml of 95% ethanol and 40 ml water was treated with 22 g of reduced electrolytic iron and 1 ml of concentrated hydrochloric acid, and the mixture was refluxed for 0.5 hr, with stirring. The resulting mixture was filtered, and the filter cake was washed with 95% ethanol. The filtrate was basified with 10% sodium hydroxide solution, extracted with dichloromethane and the organic phase was dried over anhydrous sodium sulfate, filtered, and concentrated. Purification of the residue was accomplished by preparative HPLC (Water's Associates Prep LC/System 500A, silica gel, eluted with methanol, flow rate of 200 ml/min, Gow-Mac Model 80-800 UV detector). The appropriate fractions were collected, combined and concentrated, The residue was dissolved in ether, the solution was filtered, and the filtrate was concentrated. The residue was dissolved in methanol, a few drops of ethereal hydrogen chloride was added followed by anhydrous ethyl ether dropwise until a precipitate appeared. The precipitate was collected, and the filter cake was recrystallized from methanol and anhydrous ether to afford 8.4 g of product.

Workup

  1. temperaturethe mixture was refluxed for 0.5 hr
  2. filtrationThe resulting mixture was filtered
  3. washthe filter cake was washed with 95% ethanol
  4. extractionextracted with dichloromethane
  5. dry with materialthe organic phase was dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customPurification of the residue
  9. washwas accomplished by preparative HPLC (Water's Associates Prep LC/System 500A, silica gel, eluted with methanol, flow rate of 200 ml/min, Gow-Mac Model 80-800 UV detector)
  10. customThe appropriate fractions were collected
  11. concentrationconcentrated
  12. dissolutionThe residue was dissolved in ether
  13. filtrationthe solution was filtered
  14. concentrationthe filtrate was concentrated
  15. dissolutionThe residue was dissolved in methanol
  16. additiona few drops of ethereal hydrogen chloride was added
  17. customThe precipitate was collected
  18. customthe filter cake was recrystallized from methanol and anhydrous ether

Sources & evidence

ORD record
ord-5491e4cd1d584ef3a8169e4e0115c628
Source dataset
uspto-grants-1996_04
Patent number
US05510346

Reaction notes

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