Diketene → HCID 59327641, compound

HRID 1184034Notes

Reaction equation

HRID 1184034 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH3:14])([CH3:13])[C:9]([NH:11][NH2:12])=[O:10])=[CH:4][CH:3]=1.[CH2:15]=[C:16]1[O:19][C:18](=[O:20])[CH2:17]1>O1CCCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([CH3:14])([CH3:13])[C:9]([NH:11][NH:12][C:18](=[O:20])[CH2:17][C:16](=[O:19])[CH3:15])=[O:10])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 12661DiketeneHCID 59327639HCID 59327639, compound

Product 1

HCID 59327641HCID 59327641, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-(4-chlorophenyl)-2-methylpropanehydrazide (9.0 g, 42.5 mmol) was dissolved in dry tetrahydrofuran (100 ml), and 4-methyleneoxetan-2-one (3.9 ml, 51 mmol) was added dropwise. The reaction mixture was stirred at room temperature for 18 hours, then solvent removed under resuced pressure, and ethyl acetate was added. The solution was passed through a 120 g silica gel column eluting with ethyl acetate, to provide clean N′-(2-(4-chlorophenyl)-2-methylpropanoyl)-3-oxobutanehydrazide (12.2 g, 97%) as a viscous golden oil. TLC Rf=0.47 using 100% ethyl acetate as eluent on a glass backed silica gel plate.

Workup

  1. customsolvent removed under resuced pressure, and ethyl acetate
  2. additionwas added
  3. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-a5fbbad40c0e4f87948610c9b7fd408a
Source dataset
uspto-grants-2014_03
Patent number
US08664399B2

Reaction notes

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