Hydrochloric Acid → HCID 22414365, compound

HRID 486680Notes

Reaction equation

HRID 486680 reaction equation
[CH3:1][C:2]1[S:3][CH:4]=[CH:5][C:6]=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.C(O)C.[ClH:24]>[Fe].O>[ClH:15].[ClH:24].[NH2:16][C:10]1[CH:11]=[C:12]([Cl:15])[CH:13]=[CH:14][C:9]=1[CH2:8][CH:7]([C:6]1[CH:5]=[CH:4][S:3][C:2]=1[CH3:1])[NH:19][CH3:20]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 22414394HCID 22414394, compound

Product 1

HCID 22414365HCID 22414365, compound

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent

Procedure

A mixture of 5.00 g of α-(2-methyl-3-thienyl)-N-methyl-4-chloro-2-nitrobenzeneethanamine, 9.32 g of iron powder, 100 ml of 95% ethanol, 25 ml of water, and 0.7 ml of concentrated hydrochloric acid was heated at reflux for 1.5 hr. The mixture was filtered through celite, and the organic phase was evaporated. The residue was basified with 10% aqueous sodium hydroxide, and extracted with dichloromethane. The combined organic phase was dried over anhydrous sodium sulfate, filtered and evaporated. The residue was dissolved in methanol and acidified with ethereal hydrogen chloride. The solution was diluted with ether, and the solid was collected, washed with ether, dried in vacuo, and recrystallized from methanol/ether to give 2.6 g of product, mp 242°-243° C. (dec.)

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 1.5 hr
  3. filtrationThe mixture was filtered through celite
  4. customthe organic phase was evaporated
  5. extractionextracted with dichloromethane
  6. dry with materialThe combined organic phase was dried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. customevaporated
  9. dissolutionThe residue was dissolved in methanol
  10. additionThe solution was diluted with ether
  11. customthe solid was collected
  12. washwashed with ether
  13. customdried in vacuo
  14. customrecrystallized from methanol/ether

Sources & evidence

ORD record
ord-f50a3a1df96949ce94ca69676482dfd3
Source dataset
uspto-grants-1994_03
Patent number
US05292760

Reaction notes

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