Hydrochloric Acid → HCID 20026602, compound

HRID 1723130Notes

Reaction equation

HRID 1723130 reaction equation
Cl.[CH3:2][S:3][C:4]1[N:5]([CH:9]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:10]2[CH:15]=[CH:14][C:13]([NH2:16])=[C:12]([N+:17]([O-])=O)[CH:11]=2)[CH:6]=[CH:7][N:8]=1.Cl.S1C=CC=C1.[H][H]>CO.[Pd].O>[CH3:2][S:3][C:4]1[N:5]([CH:9]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:10]2[CH:11]=[C:12]([NH2:17])[C:13]([NH2:16])=[CH:14][CH:15]=2)[CH:6]=[CH:7][N:8]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 8030ThiopheneHCID 20026596HCID 20026596, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 20026602HCID 20026602, compoundYield 100%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×HCID 962WaterSolvent

Procedure

(a-5) A mixture of 5.5 parts of (+)-4-[[2-(methylthio)-1H-imidazol-1-yl]-phenylmethyl]-2-nitrobenzenamine monohydrochloride, 24 parts of concentrated hydrochloric acid, 2 parts of a solution of thiophene in methanol 4%, 120 parts of methanol and 100 parts of water was hydrogenated at normal pressure and at 0° C. with 2 parts of palladium-on-charcoal catalyst 10%. After the calculated amount of hydrogen was taken up, the catalyst was filtered off and the filtrate was evaporated. The residue was taken up in water and treated with an ammonium hydroxide solution. The product was extracted three times with dichloromethane. The combined extracts were dried, filtered and evaporated, yielding 5.6 parts (100%) of (+)-4-[[2-(methylthio)-1H-imidazol-1-yl]phenylmethyl]-1,2-benzendiamine as a residue (int. 143).

Workup

  1. filtrationthe catalyst was filtered off
  2. customthe filtrate was evaporated
  3. additiontreated with an ammonium hydroxide solution
  4. extractionThe product was extracted three times with dichloromethane
  5. customThe combined extracts were dried
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-f0a276e840194442aba17df77a67e6e2
Source dataset
uspto-grants-1989_08
Patent number
US04859684

Reaction notes

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