Ammonium Hydroxide → HCID 69361700, compound

HRID 133085Notes

Reaction equation

HRID 133085 reaction equation
[F:1][CH:2]([F:15])[C:3](=[N:13]O)[NH:4][C:5]1[C:10]([CH3:11])=[N:9][CH:8]=[C:7]([CH3:12])[N:6]=1.[OH-].[NH4+]>OP(O)(O)=O>[F:1][CH:2]([F:15])[C:3]1[N:4]=[C:5]2[C:10]([CH3:11])=[N:9][CH:8]=[C:7]([CH3:12])[N:6]2[N:13]=1

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 178430525HCID 178430525, compound

Product 1

HCID 69361700HCID 69361700, compound

Reagents, catalysts & solvents 1

HCID 1004Phosphoric AcidSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of 2,2-difluoro-N′-hydroxy-N-(3,6-dimethylpyrazin-2-yl)ethanimidamide (3.05 g, 14.1 mmol, from Step D) and superphosphoric acid (100 mL) was heated to 130° C. with stirring for 18 h. The solution was added to ice and neutralized by addition of ammonium hydroxide. The dark aqueous solution was extracted three times with ethyl acetate, washed with brine, and dried over anhydrous magnesium sulfate. Concentration followed by flash chromatography (35% ethyl acetate/hexane) afforded the title compound as a yellow solid. LC/MS 199 (M+1).

Workup

  1. additionThe solution was added to ice
  2. extractionThe dark aqueous solution was extracted three times with ethyl acetate
  3. washwashed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationConcentration

Sources & evidence

ORD record
ord-99fcb3bd121a417091e3d7c016f3a738
Source dataset
uspto-grants-2008_06
Patent number
US07390809B2

Reaction notes

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