Methyl Stearate → N-(2,2-dimethyl-3-hydroxypropyl) stearamide

HRID 1659906

Reaction equation

HRID 1659906 reaction equation
[C:1]([O:20]C)(=O)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].[NH2:22][CH2:23][C:24]([CH3:28])([CH3:27])[CH2:25][OH:26].CC(C)([O-])C.[K+]>>[CH3:27][C:24]([CH3:28])([CH2:25][OH:26])[CH2:23][NH:22][C:1](=[O:20])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

Participants

4

Reactant 3

HCID 8201Methyl StearateHCID 1173261-Propanol, 3-amino-2,2-dimethyl-HCID 23665647Potassium tert-butoxide

Product 1

HCID 20558495N-(2,2-dimethyl-3-hydroxypropyl) stearamide

Conditions

Temperature
190 °C

Procedure

In a 500 ml, three-neck, round-bottom flask equipped with a thermometer, stirrer and a Stark and Dean trap with condenser were placed 119.4 g of methyl stearate, 41 g of 3-amino-2,2-dimethylpropanol and 3 g of potassium tert-butoxide. The mixture was heated to 190° C., and the methanol distilled off. The reaction mixture was dissolved in hot isopropanol and filtered. On cooling, the product crystallized, and after filtration and drying it melted at 44° C. IR showed an ester carbonyl. The pure product was obtained by washing with hot hexane. The pure product melted at 68°-69° C.

Workup

  1. customIn a 500 ml, three-neck, round-bottom flask equipped with a thermometer, stirrer
  2. customa Stark and Dean trap with condenser were placed
  3. distillationthe methanol distilled off
  4. dissolutionThe reaction mixture was dissolved in hot isopropanol
  5. filtrationfiltered
  6. temperatureOn cooling
  7. customthe product crystallized
  8. filtrationafter filtration
  9. customdrying it melted at 44° C
  10. customThe pure product was obtained
  11. washby washing with hot hexane

Sources & evidence

ORD record
ord-e88f5d4d94e04b4596963e171c13e3cf
Source dataset
uspto-grants-1981_12
Patent number
US04305868

Linked notes

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