Ammonium Chloride → Hydrochloric Acid

HRID 1462112Notes

Reaction equation

HRID 1462112 reaction equation
[N+:1]([C:4]1[CH:29]=[CH:28][C:7]([CH2:8][S:9][CH:10]([S:17][CH2:18][C:19]2[CH:24]=[CH:23][C:22]([N+:25]([O-])=O)=[CH:21][CH:20]=2)[CH2:11][N:12]2[CH:16]=[CH:15][N:14]=[CH:13]2)=[CH:6][CH:5]=1)([O-])=O.[Cl-:30].[NH4+]>O.C(O)C.[Fe]>[ClH:30].[ClH:30].[ClH:30].[ClH:30].[NH2:25][C:22]1[CH:23]=[CH:24][C:19]([CH2:18][S:17][CH:10]([S:9][CH2:8][C:7]2[CH:28]=[CH:29][C:4]([NH2:1])=[CH:5][CH:6]=2)[CH2:11][N:12]2[CH:16]=[CH:15][N:14]=[CH:13]2)=[CH:20][CH:21]=1

Participants

7

Reactant 2

HCID 25517Ammonium ChlorideHCID 13320337HCID 13320337, compound

Product 2

HCID 313Hydrochloric AcidHCID 20454623HCID 20454623, compound

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A stirred mixture of 1-[2,2-bis(4-nitrobenzylthio)ethyl]-1H-imidazole (924 mg), iron powder (1.08 g) and ammonium chloride (862 mg) in water (30 ml) was refluxed for 2 hours. The cooled mixture was thoroughly extracted with CH2Cl2 and the combined CH2Cl2 extracts were washed with water and dried over Na2SO4. Removal of the CH2Cl2 left 360 mgs. of the crude amine as a viscous oil. The black residue, which resisted extraction with CH2Cl2, was extracted with dilute aqueous oxalic acid. The aqueous mixture was filtered, and the filtrate was made basic with aqueous potassium hydroxide. Extraction of the filtrate with CH2Cl2 gave another crop of the crude amine which was combined with the 360 mg. fraction. The crude amine was chromatographed on silicic acid (20 g) with CH2Cl2 /CH3OH/diethyl amine (500:25:2) to afford 340 mg. of the pure amine. Treatment of a solution of the pure base in ethanol with hydrogen chloride afforded the title compound as a light tan amorphous solid which melted indistinctly with decomposition.

Workup

  1. temperaturewas refluxed for 2 hours
  2. extractionThe cooled mixture was thoroughly extracted with CH2Cl2
  3. washthe combined CH2Cl2 extracts were washed with water
  4. dry with materialdried over Na2SO4
  5. customRemoval of the CH2Cl2
  6. waitleft 360 mgs
  7. extractionextraction with CH2Cl2
  8. extractionwas extracted with dilute aqueous oxalic acid
  9. filtrationThe aqueous mixture was filtered
  10. extractionExtraction of the filtrate with CH2Cl2
  11. customgave another crop of the crude amine which
  12. customThe crude amine was chromatographed on silicic acid (20 g) with CH2Cl2 /CH3OH/diethyl amine (500:25:2)
  13. customto afford 340 mg

Sources & evidence

ORD record
ord-0537ae8f15d342418ddf1d4c2fdeef80
Source dataset
uspto-grants-1984_07
Patent number
US04458079

Reaction notes

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