4Iodo-benzoic acid N'-(2,2-dimethyl-propionyl)-hydrazide → 4-Iodobenzenecarbohydrazide

HRID 31410

Reaction equation

HRID 31410 reaction equation
CC(C)(C)C([NH:5][NH:6][C:7](=[O:15])[C:8]1[CH:13]=[CH:12][C:11]([I:14])=[CH:10][CH:9]=1)=O>FC(F)(F)C(O)=O>[I:14][C:11]1[CH:12]=[CH:13][C:8]([C:7]([NH:6][NH2:5])=[O:15])=[CH:9][CH:10]=1

Participants

3

Reactant 1

HCID 693159064Iodo-benzoic acid N'-(2,2-dimethyl-propionyl)-hydrazide2×

Product 1

HCID 3061044-Iodobenzenecarbohydrazide

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

Trifluoroacetic acid (10 ml) was added to 4iodo-benzoic acid N′-(2,2-dimethyl-propionyl)-hydrazide (Intermediate 13) (1 g, 2.76 mmol) and stirred at room temperature for 2 hours. The trifluoroactic acid was removed in vacuo and the residue partitioned between ethyl acetate (50 ml) and saturated aqueous sodium bicarbonate solution (50 ml). The organic layer was washed with water (50 ml), brine (50 ml), dried over magnesium sulfate, filtered and the solvent removed in vacuo. The desired product was obtained as a white solid (0.55 g, 2.1 mmol).

Workup

  1. customThe trifluoroactic acid was removed in vacuo
  2. customthe residue partitioned between ethyl acetate (50 ml) and saturated aqueous sodium bicarbonate solution (50 ml)
  3. washThe organic layer was washed with water (50 ml), brine (50 ml)
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-ac02ab09da504815b72b4796a3df3564
Source dataset
uspto-grants-2008_09
Patent number
US07425555B2

Linked notes

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