HCID 178425639, compound → HCID 178424057, compound

HRID 1619140Notes

Reaction equation

HRID 1619140 reaction equation
[NH:1]=[C:2]([C:10]1[CH:15]=[CH:14][C:13]([CH3:16])=[C:12]([I:17])[CH:11]=1)[NH:3][NH:4][C:5]([CH:7]1[CH2:9][CH2:8]1)=O>P(Cl)(Cl)(Cl)=O>[CH:7]1([C:5]2[NH:1][C:2]([C:10]3[CH:15]=[CH:14][C:13]([CH3:16])=[C:12]([I:17])[CH:11]=3)=[N:3][N:4]=2)[CH2:9][CH2:8]1

Participants

3

Reactant 1

HCID 178425639HCID 178425639, compound

Product 1

HCID 178424057HCID 178424057, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Procedure

A solution of N′-(imino(3-iodo-4-methylphenyl)methyl)cyclopropanecarbohydrazide (preparation 51c, 0.76 g, 2.2 mmol) in phosphorus oxychloride (10 mL) was heated in a sealed tube at 110° C. with stirring. After 14 hours, the mixture was cooled and concentrated in vacuo. Ethyl acetate and saturated aqueous sodium hydrogen carbonate solution were added to the residue. The organic layer was dried (MgSO4) and evaporated in vacuo. The residue was purified by flash chromatography (2:1 hexanes/ethyl acetate) to give the title compound (0.14 g, 20%) as a white solid.

Workup

  1. temperaturethe mixture was cooled
  2. concentrationconcentrated in vacuo
  3. additionEthyl acetate and saturated aqueous sodium hydrogen carbonate solution were added to the residue
  4. dry with materialThe organic layer was dried (MgSO4)
  5. customevaporated in vacuo
  6. customThe residue was purified by flash chromatography (2:1 hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-24f5f5f5a04044848b78e5d690c5339a
Source dataset
uspto-grants-2014_07
Patent number
US08772288B2

Reaction notes

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