Ethyl Acetate → 1-Methylpropyl 2-(3-phenoxyphenyl)hydrazine carboxylate

HRID 379075Notes

Reaction equation

HRID 379075 reaction equation
[O:1]([C:8]1[CH:9]=[C:10]([NH:14][NH2:15])[CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(OCC)(=O)C.Cl[C:23]([O:25][CH:26]([CH2:28][CH3:29])[CH3:27])=[O:24]>N1C=CC=CC=1>[O:1]([C:8]1[CH:9]=[C:10]([NH:14][NH:15][C:23]([O:25][CH:26]([CH3:27])[CH2:28][CH3:29])=[O:24])[CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 11829505sec-Butyl chloroformateHCID 21697795(3-Phenoxyphenyl)hydrazine

Product 1

HCID 216977971-Methylpropyl 2-(3-phenoxyphenyl)hydrazine carboxylate

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To 3.0 g of 3-phenoxyphenyl hydrazine, 100 ml of ethyl acetate and 2.5 ml of pyridine were added and the resultant solution was then stirred at room temperature for 30 minutes. Then, 2.5 ml of sec-butyl chloro-formate was added dropwise to the solution and stirred for 1 hour at room temperature. The solution was then washed twice, each time with 100 ml of water. After each wash, the aqueous fraction was removed from the organic (ethyl acetate) fraction. The resulting ethyl acetate fraction was then dried over anhydrous sodium sulfate, evaporated under reduced pressure, and then purified by column chromatography on silica gel, to produce 1.5 g of 1-methylpropyl 2-(3-phenoxyphenyl)hydrazine carboxylate as an oil.

Workup

  1. washThe solution was then washed twice
  2. customAfter each wash, the aqueous fraction was removed from the organic (ethyl acetate) fraction
  3. dry with materialThe resulting ethyl acetate fraction was then dried over anhydrous sodium sulfate
  4. customevaporated under reduced pressure
  5. custompurified by column chromatography on silica gel

Sources & evidence

ORD record
ord-3091d23f772d4576837ca4b5f6f655b4
Source dataset
uspto-grants-2001_10
Patent number
US06297275B1

Reaction notes

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