Acetic Acid → HCID 67495222, compound

HRID 658563Notes

Reaction equation

HRID 658563 reaction equation
[C:1]([O:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)(=[O:4])[NH:2][NH2:3].[CH:13]1([CH:19]=O)[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1.C(O)(=O)C>C(O)C>[CH2:6]([O:5][C:1]([NH:2][N:3]=[CH:19][CH:13]1[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1)=[O:4])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 16275CyclohexanecarboxaldehydeHCID 79242Benzyl carbazate

Product 1

HCID 67495222HCID 67495222, compoundYield 73.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Benzyl carbazate (25 g, 150.44 mmoles) was dissolved in 200 mL ethanol under a nitrogen atmosphere in a round bottom flask equipped with magnetic stirring. Cyclohexanecarbaldehyde (17.7 g, 158 mmoles) and acetic acid (1 mL) were added to the solution and the mixture was stirred at room temperature for 8 h. The resultant solid precipitate was filtered, washed with hexanes, crystallized from ethyl acetate, and dried overnight on the open bench to provide 28.87 g (73.7% yield) white crystalline N′-cyclohexylmethylene-hydrazinecarboxylic acid benzyl ester. Rf=0.67 (1:3 hexanes:ethyl acetate), 1H NMR (400 MHz, CDCl3) δ 7.8 (1H, br s), 7.4 (5H, m), 7.1 (1H, br s), 5.3 (2H, s), 2.4 (1H, m), 1.7-1.9 (4H, m), 1.3 (6H, m); HRMS (ESI) m/z calcd for C15H21N2O2 [M+H]+ 261.1603, found 261.1592, calcd for C15H20NaN2O2 [M+Na]+ 283.1426, found 283.1417.

Workup

  1. customequipped with magnetic stirring
  2. filtrationThe resultant solid precipitate was filtered
  3. washwashed with hexanes
  4. customcrystallized from ethyl acetate
  5. customdried overnight on the open bench

Sources & evidence

ORD record
ord-f3acef210ab641ec884b26198629a0cf
Source dataset
uspto-grants-2011_12
Patent number
US08076517B2

Reaction notes

Loading…