Acetic Acid → HCID 86631998, compound

HRID 335664Notes

Reaction equation

HRID 335664 reaction equation
[CH3:1][C:2]([CH:5]=O)([CH3:4])[CH3:3].C(O)(=O)C.[C:11]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])(=[O:14])[NH:12][NH2:13]>CO>[C:16]([O:15][C:11]([NH:12][N:13]=[CH:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:14])([CH3:19])([CH3:18])[CH3:17]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 12417PivalaldehydeHCID 70091tert-Butyl carbazate

Product 1

HCID 86631998HCID 86631998, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Pivaldehyde (52.1 g, 454 mmoles, ca. 75% solution in t-butanol) was dissolved in 120 mL methanol in a 1 L, 3-necked round bottom flask with reflux condenser, thermometer, and addition funnel. Glacial acetic acid (1 mL) was added followed by controlled addition of t-butyl carbazate (50 g, 378 mmoles), without removal of heat of the reaction. The mixture was stirred for 4 hours, while monitoring by TLC. Upon completion of the reaction, the solvent was removed in vacuo, the residue was taken up in pentane, and the pentane was evaporated. The resultant oil crystallized upon standing to provide N′-(2,2-dimethyl-propylidene)-hydrazinecarboxylic acid tert-butyl ester (75.7 g, 93%). Rf=0.42 (2:1 hexanes:ethyl acetate, 1% acetic acid); 1H NMR (400 MHz, CDCl3) δ 7.6 (br s, 1H), 7.1 (s, 1H), 1.5 (s, 9H), 1.1 (s, 9H) ppm.

Workup

  1. temperaturewith reflux condenser
  2. additionthermometer, and addition funnel
  3. temperatureof heat of the reaction
  4. customUpon completion of the reaction
  5. customthe solvent was removed in vacuo
  6. customthe pentane was evaporated
  7. customThe resultant oil crystallized

Sources & evidence

ORD record
ord-feff8a1354d148a88464cded92b04063
Source dataset
uspto-grants-2014_11
Patent number
US08884060B2

Reaction notes

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