Methyl Ethyl Ketone → 2-(1-Methylpropylidene)hydrazinecarboxamide

HRID 1880352Notes

Reaction equation

HRID 1880352 reaction equation
Cl.[NH2:2][NH:3][C:4]([NH2:6])=[O:5].[CH2:7]([C:9]([CH3:11])=O)[CH3:8].C([O-])(=O)C.[Na+]>O>[CH3:8][C:7](=[N:2][NH:3][C:4]([NH2:6])=[O:5])[CH2:9][CH3:11]

Participants

5

Reactant 3

HCID 6569Methyl Ethyl KetoneHCID 11236Semicarbazide hydrochlorideHCID 517045Sodium Acetate

Product 1

HCID 122132-(1-Methylpropylidene)hydrazinecarboxamideYield 72%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of semicarbazide HCl (61.2 g, 534 mmol), ethyl-methyl ketone (35 g, 0.49 mol) in water (525 mL), sodium acetate (79.7 g, 972 mmol) was added at room temperature and maintained for 18 hours. The reaction mixture was filtered, the obtained solid was washed with ether (2×25 mL) and dried at 70° C. for 20 hours to afford butan-2-one semicarbazone (45 g, 72%) as white solid. 1H NMR (CDCl3) δ 7.9 (br, 1H), 5.0-6.0 (br, 2H), 2.3 (q, 2H), 1.82 (s, 3H), 1.1 (t, 3H).

Workup

  1. temperaturemaintained for 18 hours
  2. filtrationThe reaction mixture was filtered
  3. washthe obtained solid was washed with ether (2×25 mL)
  4. customdried at 70° C. for 20 hours

Sources & evidence

ORD record
ord-35a6387c9f4c4c2283a52a9275c9de67
Source dataset
uspto-grants-2012_11
Patent number
US08318762B2

Reaction notes

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