Sodium Chloride → HCID 14580243, compound

HRID 1761724Notes

Reaction equation

HRID 1761724 reaction equation
[CH3:1][O:2][C:3]([NH:5][CH2:6][C:7]([O:9][CH3:10])=[O:8])=[O:4].[H-].[Na+].[CH2:13](Cl)[C:14]#[CH:15].[Cl-].[Na+]>CN(C)C=O>[CH2:15]([N:5]([C:3]([O:2][CH3:1])=[O:4])[CH2:6][C:7]([O:9][CH3:10])=[O:8])[C:14]#[CH:13]

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 122213-Chloro-1-propyneHCID 24758Sodium hydrideHCID 14133519HCID 14133519, compound

Product 1

HCID 14580243HCID 14580243, compoundYield 51.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3.0 g of methyl N-methoxycarbonylglycinate were dissolved in 30 ml of N,N-dimethylformamide. Ice-cooling the mixture, 820 g of sodium hydride (60% oil dispersion) were added thereto under a nitrogen atmosphere and stirred for 20 minutes. Then 2.3 g of propargyl chloride were dropped thereto over 10 minutes and further stirred for 40 minutes. The reaction mixture was poured into ice-water and then sodium chloride was added thereto to saturate the same. Thereafter the aqueous layer was washed with hexane and it was subjected to two times of extraction with 100 ml of ether. The ether layers were combined together and dried over anhydrous magnesium sulfate and the solvent was evaporated off to obtain 1.95 g of methyl N-propargyl-N-methoxycarbonylglycinate.

Workup

  1. additionwere added
  2. waitover 10 minutes
  3. stirringfurther stirred for 40 minutes
  4. concentrationto saturate the same
  5. washThereafter the aqueous layer was washed with hexane and it
  6. extractionwas subjected to two times of extraction with 100 ml of ether
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customthe solvent was evaporated off

Sources & evidence

ORD record
ord-1462714f42824de590dc8a3b24e429be
Source dataset
uspto-grants-1989_05
Patent number
US04827020

Reaction notes

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