1-benzyl-4-nitro-1H-imidazole-5-sulfonamide → 4-amino-1-benzyl-1H-imidazole-5-sulfonamide

HRID 601300Notes

Reaction equation

HRID 601300 reaction equation
[CH2:1]([N:8]1[C:12]([S:13]([NH2:16])(=[O:15])=[O:14])=[C:11]([N+:17]([O-])=O)[N:10]=[CH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(O)(=O)C.O1CCOCC1.[Fe]>[NH2:17][C:11]1[N:10]=[CH:9][N:8]([CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[C:12]=1[S:13]([NH2:16])(=[O:15])=[O:14]

Participants

5

Reactant 1

HCID 125360111-benzyl-4-nitro-1H-imidazole-5-sulfonamide

Product 1

HCID 125691424-amino-1-benzyl-1H-imidazole-5-sulfonamideYield 46.3%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 176Acetic AcidSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
25 °C

Procedure

A solution of the product of Example 312E (434 mg, 1.54 mmol) in acetic acid (4.3 mL) and dioxane (4.3 mL) was reacted with iron powder (343 mg, 6.15 mmol) at 50° C. for 3 hours. The reaction mixture was cooled to 25° C., filtered through a pad of celite® (diatomaceous earth) and the filtrate was concentrated under reduced pressure. The residue was dissolved in dichloromethane and washed with a saturated aqueous sodium bicarbonate solution. The aqueous layer was extracted with dichloromethane (2×) and the combined organic layers were dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was chromatographed on silica gel using a gradient of methanol in dichloromethane (0-5%) to give the title compound (180 mg, 46%). MS (ESI+) m/z 253 (M+H)+. 1H NMR (300 MHz, DMSO-d6) δ ppm 5.24 (s, 2H), 7.22-7.39 (m, 5H), 7.43 (s, 1H).

Workup

  1. filtrationfiltered through a pad of celite® (diatomaceous earth)
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. dissolutionThe residue was dissolved in dichloromethane
  4. washwashed with a saturated aqueous sodium bicarbonate solution
  5. extractionThe aqueous layer was extracted with dichloromethane (2×)
  6. dry with materialthe combined organic layers were dried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was chromatographed on silica gel using a gradient of methanol in dichloromethane (0-5%)

Sources & evidence

ORD record
ord-aa6bee074f4c4912831ee92047f55540
Source dataset
uspto-grants-2011_03
Patent number
US07902203B2

Reaction notes

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