Sodium Carbonate → 2,6-Difluoro-N-hydroxy-N-methyl-benzamidine

HRID 1822683Notes

Reaction equation

HRID 1822683 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([F:10])[C:3]=1[C:4]#[N:5].Cl.[CH3:12][NH:13][OH:14].C(=O)([O-])[O-].[Na+].[Na+]>O.C(O)C>[F:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([F:10])[C:3]=1[C:4]([N:13]([OH:14])[CH3:12])=[NH:5]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 746952,6-DifluorobenzonitrileHCID 77906N-methylhydroxylamine hydrochloride

Product 1

HCID 221696372,6-Difluoro-N-hydroxy-N-methyl-benzamidineYield 100.7%

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Conditions

Temperature
100 °C

Procedure

To a stirred solution of 2,6-difluorobenzonitrile (5.565 g, 40 mmol) and N-methylhydroxylamine hydrochloride (10 g, 120 mmol) in 4:1 water/ethanol (100 mL) was added sodium carbonate (8.5 g, 80 mmol) in small portions and the resulting mixture stirred at 100° C. for 2 h. The mixture was then cooled, concentrated and the resulting residue suspended in hot MeOH/CHCl3 (1:9, 200 mL). The insoluble solids were removed by filtration and concentration of the filtrate gave the desired product as an off-white solid (7.50 g, 100% yield). 1HNMR (500 MHz, DMSO-d6) δ: 7.69–7.63 (1H, m), 7.29 (2H, t, J=8.24 Hz), 6.90 (2H, s), 3.15 (3H, s). LCMS calcd for C8H9F2N2O (M+H): 187.07; found: 187.12.

Workup

  1. temperatureThe mixture was then cooled
  2. concentrationconcentrated
  3. customThe insoluble solids were removed by filtration and concentration of the filtrate

Sources & evidence

ORD record
ord-d2e454cb6e874a268aa6f4b36b2e0f60
Source dataset
uspto-grants-2006_05
Patent number
US07037908B2

Reaction notes

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