Methyl chloroacetate → HCID 17834761, compound

HRID 491237Notes

Reaction equation

HRID 491237 reaction equation
[CH2:1]([O:23][CH2:24][CH2:25][CH2:26][NH2:27])[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][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22].[Cl:28][CH2:29][C:30](OC)=[O:31]>CO.C[O-].[Na+]>[Cl:28][CH2:29][C:30]([NH:27][CH2:26][CH2:25][CH2:24][O:23][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][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])=[O:31]

Participants

5

Reactant 2

HCID 7295Methyl chloroacetateHCID 13272234HCID 13272234, compound

Product 1

HCID 17834761HCID 17834761, compoundYield 94%

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 383.69 g of 3-docosyloxypropylamine obtained in the same manner as in Example 24, 1000 g of methanol and 9.6 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 20 to 30° C. and the resulting mixture was reacted for 24 hours. After the reaction was completed, the precipitated crystal was filtered. The crystal was washed with 1000 g of methanol and then dried to obtain 432.6 g of 2-chloro-N-(3-docosyloxypropyl)-acetamide as a white powder.

Workup

  1. customA four-necks-flask equipped with a stirrer
  2. customwas kept at 20 to 30° C.
  3. customthe resulting mixture was reacted for 24 hours
  4. filtrationthe precipitated crystal was filtered
  5. washThe crystal was washed with 1000 g of methanol
  6. customdried

Sources & evidence

ORD record
ord-f67185758cdd4f31b3eccc784779ccaf
Source dataset
uspto-grants-2009_05
Patent number
US07531165B2

Reaction notes

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