Acetic Acid → HCID 67495222, compound

HRID 335672Notes

Reaction equation

HRID 335672 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-cbaa21b1e8ff48898400be0282cb46ce
Source dataset
uspto-grants-2014_11
Patent number
US08884060B2

Reaction notes

Loading…