Hydroxyamine hydrochloride → HCID 178526378, compound

HRID 605895Notes

Reaction equation

HRID 605895 reaction equation
[Br:1][C:2]1[C:3]([N:9]=[CH:10][N:11](C)C)=[N:4][C:5]([Br:8])=[CH:6][N:7]=1.Cl.N[OH:16]>CO>[Br:1][C:2]1[C:3]([NH:9][CH:10]=[N:11][OH:16])=[N:4][C:5]([Br:8])=[CH:6][N:7]=1

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 57589986N'-(3,6-dibromopyrazin-2-yl)-n,n-dimethyl-formamidine

Product 1

HCID 178526378HCID 178526378, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of N′-(3,6-dibromo-pyrazin-2-yl)-N,N-dimethylformamidine (18.6 g, 60.80 mmol) in methanol (200 mL) is added hydroxylamine hydrochloride (5.91 g, 85.12 mmol) in one portion. The reaction is stirred at room temperature for 16 hours. The solvent is evaporated and the solid residue is treated with cold (ice cooling) water and collected by filtration. The precipitate is washed twice with water and petroleum ether and dried in vacuo yielding the title compound (17.45 g) as a white solid. 1H-NMR (400 MHz, d6-DMSO) δ (ppm) 7.82 (1H, br s), 8.21 (1H, s), 8.34 (1H, m), 11.17 (1H, br s). LCMS: Rt 3.17 min (98.7%), m/z (APCI) 295 (M+H)+.

Workup

  1. customThe solvent is evaporated
  2. additionthe solid residue is treated with cold (ice cooling) water
  3. filtrationcollected by filtration
  4. washThe precipitate is washed twice with water and petroleum ether
  5. customdried in vacuo

Sources & evidence

ORD record
ord-289f87d833c4418ab97520a667be27f5
Source dataset
uspto-grants-2011_03
Patent number
US07915256B2

Reaction notes

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