Ammonium Chloride → HCID 21897393, compound

HRID 719872Notes

Reaction equation

HRID 719872 reaction equation
[N+:1]([C:4]1[N:5]=[CH:6][C:7]([NH:10][S:11]([CH3:14])(=[O:13])=[O:12])=[N:8][CH:9]=1)([O-])=O.[Cl-].[NH4+]>CO.O.[Zn]>[NH2:1][C:4]1[N:5]=[CH:6][C:7]([NH:10][S:11]([CH3:14])(=[O:13])=[O:12])=[N:8][CH:9]=1

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 21897390N-(5-nitro-pyrazin-2-yl)-methanesulfonamide

Product 1

HCID 21897393HCID 21897393, compoundYield 109.2%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
25 °C

Procedure

A solution of N-(5-nitro-pyrazin-2-yl)-methanesulfonamide (583.9 mg, 2.67 mmol) in methanol (26.8 mL) was treated with a solution of ammonium chloride (300.6 mg, 5.62 mmol) in water (2 mL). This solution was stirred at 25° C. for 5 min. At this time, the reaction was treated with zinc dust (1.71 g, 26.2 mmol). The resulting mixture was heated under reflux for 2 h. At this time, the reaction was cooled to 25° C. and was filtered through a pad of silica gel (9/1 methylene chloride/methanol wash). The filtrate was concentrated in vacuo to afford N-(5-amino-pyrazin-2-yl)-methanesulfonamide (548.8 mg, 100%) as a dark-brown gum: EI-HRMS m/e calcd for C5H8N4O2S (M+H)+ 189.0441, found 189.0442.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureunder reflux for 2 h
  3. temperatureAt this time, the reaction was cooled to 25° C.
  4. filtrationwas filtered through a pad of silica gel (9/1 methylene chloride/methanol wash)
  5. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-a901d0deaa1c4cb0a929fefb77e56629
Source dataset
uspto-grants-2006_11
Patent number
US07132425B2

Reaction notes

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