Methyl chloroacetate → 2-chloro-N-(3-octadecyloxypropyl)-acetamide

HRID 491238Notes

Reaction equation

HRID 491238 reaction equation
[CH2:1]([O:19][CH2:20][CH2:21][CH2:22][NH2:23])[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].[Cl:24][CH2:25][C:26](OC)=[O:27]>CO.C[O-].[Na+]>[Cl:24][CH2:25][C:26]([NH:23][CH2:22][CH2:21][CH2:20][O:19][CH2:1][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])=[O:27]

Participants

5

Reactant 2

HCID 7295Methyl chloroacetateHCID 820871-Propanamine, 3-(octadecyloxy)-

Product 1

HCID 178347642-chloro-N-(3-octadecyloxypropyl)-acetamideYield 92%

Reagents, catalysts & solvents 2

HCID 887MethanolCatalyst2×HCID 10942334Sodium MethoxideCatalyst

Procedure

A four-necks-flask equipped with a stirrer, a temperature gage, a dehydrating pipe and a dropping funnel was charged with 327.6 g of 3-octadecyloxypropylamine obtained in the same manner as in Example 21, 900 g of methanol and 3.9 g of a methanol solution of 28% sodium methylate as a catalyst. 113.9 g of methyl chloroacetate was added to the mixture in one hour while the mixture was kept at 15 to 25° C. and the resulting mixture was reacted for 30 hours. After the reaction was completed, the precipitated crystal was filtered. The crystal was washed with 300 g of methanol and then dried to obtain 371.8 g of 2-chloro-N-(3-octadecyloxypropyl)-acetamide as a white powder.

Workup

  1. customA four-necks-flask equipped with a stirrer
  2. customwas kept at 15 to 25° C.
  3. customthe resulting mixture was reacted for 30 hours
  4. filtrationthe precipitated crystal was filtered
  5. washThe crystal was washed with 300 g of methanol
  6. customdried

Sources & evidence

ORD record
ord-2759aafdfff3481884a10afd24c5f8a9
Source dataset
uspto-grants-2009_05
Patent number
US07531165B2

Reaction notes

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