Sodium Hydroxide → HCID 66953683, compound

HRID 2096984Notes

Reaction equation

HRID 2096984 reaction equation
[CH:1]1([NH:4][C:5]([NH:7][NH:8][C:9]2[C:14]([I:15])=[CH:13][CH:12]=[CH:11][N:10]=2)=O)[CH2:3][CH2:2]1.P(Cl)(Cl)(Cl)=O.[OH-].[Na+]>>[CH:1]1([NH:4][C:5]2[N:10]3[CH:11]=[CH:12][CH:13]=[C:14]([I:15])[C:9]3=[N:8][N:7]=2)[CH2:3][CH2:2]1

Participants

4

Reactant 3

HCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 66954038HCID 66954038, compound

Product 1

HCID 66953683HCID 66953683, compoundYield 92.6%

Conditions

Temperature
75 °C

Procedure

A mixture of N-cyclopropyl-2-(3-iodopyridin-2-yl)hydrazinecarboxamide (preparation 26c, 0.56 g, 1.8 mmol) and phosphorous oxychloride (7 mL) was stirred at 75° C. overnight. The reaction mixture was cooled to ambient temperature, added slowly to an ice-water mixture and then was basified to pH 8 with aqueous sodium hydroxide solution. The aqueous solution was extracted with ethyl acetate and the organic layer was washed with brine, dried (MgSO4) and the solvent evaporated in vacuo to yield the title compound (0.50 g, 88%) as a solid.

Workup

  1. temperatureThe reaction mixture was cooled to ambient temperature
  2. extractionThe aqueous solution was extracted with ethyl acetate
  3. washthe organic layer was washed with brine
  4. dry with materialdried (MgSO4)
  5. customthe solvent evaporated in vacuo

Sources & evidence

ORD record
ord-19b793305f8c4aa78f1be84d0a8b11ef
Source dataset
uspto-grants-2013_05
Patent number
US08450341B2

Reaction notes

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