Triethylamine → HCID 19370295, compound

HRID 129756Notes

Reaction equation

HRID 129756 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[CH2:6]([O:8][C:9]([N:11]([CH2:13][CH2:14][OH:15])[CH3:12])=[O:10])[CH3:7].C(N(CC)CC)C>C(Cl)Cl>[CH3:1][S:2]([O:15][CH2:14][CH2:13][N:11]([C:9]([O:8][CH2:6][CH3:7])=[O:10])[CH3:12])(=[O:4])=[O:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 1937035525450-10-6

Product 1

HCID 19370295HCID 19370295, compoundYield 103.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1.65 g of methanesulfonyl chloride was added dropwise, with stirring, to a solution of 1.66 g of 2-(N-ethoxycarbonyl-N-methylamino)ethanol and 1.65 g of triethylamine in 20 ml of methylene chloride, whilst ice-cooling, and the solution was then stirred at the same temperature for 30 minutes. At the end of this time, the mixture was poured into ice-water and extracted with methylene chloride. The extracts were combined and washed with water, after which they were dried over anhydrous sodium sulfate. Evaporation of the solvent under reduced pressure gave a residue which was purified by column chromatography through silica gel, using a 2:1 by volume mixture of ethyl acetate and hexane as the eluent, to give 2.62 g (yield 81%) of the title compound as an oil.

Workup

  1. temperaturecooling
  2. extractionextracted with methylene chloride
  3. washwashed with water
  4. dry with materialafter which they were dried over anhydrous sodium sulfate
  5. customEvaporation of the solvent under reduced pressure
  6. customgave a residue which
  7. customwas purified by column chromatography through silica gel
  8. additionby volume mixture of ethyl acetate and hexane as the eluent

Sources & evidence

ORD record
ord-d7fbf0c63ccd48629c71ca48031e669e
Source dataset
uspto-grants-1995_11
Patent number
US05470851

Reaction notes

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