Acetone → Octadecanamide, N-methyl-

HRID 1779875Notes

Reaction equation

HRID 1779875 reaction equation
CC(C)=O.CN.[C:7](Cl)(=[O:25])[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24].[CH2:27]([N:29](CC)CC)C>O>[CH3:27][NH:29][C:7](=[O:25])[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24]

Participants

6

Reactant 4

HCID 180AcetoneHCID 6329MethylamineHCID 8212Stearoyl chlorideHCID 8471Triethylamine

Product 1

HCID 519746Octadecanamide, N-methyl-

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 500 cc of acetone was added 15.5 g of methylamine to form a mixture. 60.0 g of stearoyl chloride was drop-wise added to the mixture, while the mixture was stirred and cooled using ice water. The addition was conducted at a temperature of not higher than 20° C. Further, 20.2 g of triethylamine was dropwise added to the mixture at a temperature of not higher than 20° C. After the addition was complete, the mixture was allowed to react for 3 hours. The reaction mixture was then poured into water and the aqueous mixture was filtered to collect produced crystals, and the crystals were recrystallized from a mixed solvent of ethyl acetate and methanol to give a white crystalline product of N-methylstearic amide (Amide compound No. 1 mentioned above).

Workup

  1. customto form a mixture
  2. temperaturecooled
  3. additionThe addition
  4. customhigher than 20° C
  5. additionAfter the addition
  6. customto react for 3 hours
  7. filtrationthe aqueous mixture was filtered
  8. customto collect
  9. customproduced crystals
  10. customthe crystals were recrystallized from a mixed solvent of ethyl acetate and methanol

Sources & evidence

ORD record
ord-162467f3120a41db8727d5dc1044566f
Source dataset
uspto-grants-1997_05
Patent number
US05629129

Reaction notes

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