Acetic Acid → HCID 86631998, compound

HRID 658555Notes

Reaction equation

HRID 658555 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-7f5f036e21fa46b09b6acdba65094fcd
Source dataset
uspto-grants-2011_12
Patent number
US08076517B2

Reaction notes

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