Ammonium Chloride → HCID 20446275, compound

HRID 2418337Notes

Reaction equation

HRID 2418337 reaction equation
[Cl-].[NH4+].[N+:3]([C:6]1[C:11]([S:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:10][CH:9]=[CH:8][C:7]=1[CH2:19][C:20]([O:22]CC)=O)([O-])=O>C(O)C.O.[Fe]>[O:22]=[C:20]1[CH2:19][C:7]2[C:6](=[C:11]([S:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH:10]=[CH:9][CH:8]=2)[NH:3]1

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 20446162HCID 20446162, compound

Product 1

HCID 20446275HCID 20446275, compound

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A suspension of iron powder (1.5 g.) and ammonium chloride (0.15 g.) in a mixture of ethanol (7 ml.) and water (7ml.) was refluxed with stirring. Ethyl 2-(2-nitro-3-phenylthiophenyl)acetate (1.6 g.) was added to the suspension, and the mixture was refluxed for 7 hours and filtered. The filtrate was evaporated to dryness under reduced pressure, and residue was dissolved in ethyl acetate. The solution was washed with water, dried over magnesium sulfate and evaporated under reduced pressure. The oily residue was dissolved in ethanol (10 ml.) and heated with conc. hydrochloric acid (0.1 ml.). The precipitating crystals were collected by filtration and dried to give the captioned compound (0.9 g.). mp 160° to 161° C.

Workup

  1. temperaturewas refluxed
  2. temperaturethe mixture was refluxed for 7 hours
  3. filtrationfiltered
  4. customThe filtrate was evaporated to dryness under reduced pressure, and residue
  5. dissolutionwas dissolved in ethyl acetate
  6. washThe solution was washed with water
  7. dry with materialdried over magnesium sulfate
  8. customevaporated under reduced pressure
  9. dissolutionThe oily residue was dissolved in ethanol (10 ml.)
  10. temperatureheated with conc. hydrochloric acid (0.1 ml.)
  11. filtrationThe precipitating crystals were collected by filtration
  12. customdried
  13. customto give the captioned compound (0.9 g.)

Sources & evidence

ORD record
ord-920773cd8e304bf29450404ec9499d6e
Source dataset
uspto-grants-1984_09
Patent number
US04472433

Reaction notes

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