Triethylamine → HCID 19079087, compound

HRID 2210093Notes

Reaction equation

HRID 2210093 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][NH:6][C:7](=[O:15])[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14].C(N(CC)CC)C.[CH3:23][S:24](Cl)(=[O:26])=[O:25]>C(Cl)Cl>[CH3:23][S:24]([O:1][CH2:2][CH2:3][CH2:4][CH2:5][NH:6][C:7](=[O:15])[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])(=[O:26])=[O:25]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 19079213HCID 19079213, compound

Product 1

HCID 19079087HCID 19079087, compoundYield 105.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2.00 g (8.22 mmol) of N-(4-hydroxybutyl)caprylamide and 1.37 ml (9.86 mmol) of triethylamine in 50 ml of methylene chloride was added 0.76 ml (9.86 mmol) of methanesulfonyl chloride under ice-cooling with stirring. The mixture was stirred at room temperature for 30 minutes. The reaction mixture was washed with an aqueous saturated sodium bicarbonate solution and water and dried. The solvent was distilled off. The residue was washed with hexane to obtain 2.55 g of the desired compound (96.5% colorless powder), mp: 59.0°-60.0° C.

Workup

  1. temperaturecooling
  2. stirringThe mixture was stirred at room temperature for 30 minutes
  3. washThe reaction mixture was washed with an aqueous saturated sodium bicarbonate solution and water
  4. customdried
  5. distillationThe solvent was distilled off
  6. washThe residue was washed with hexane

Sources & evidence

ORD record
ord-885d43cbe2dd49788542d517a9387ddc
Source dataset
uspto-grants-1995_10
Patent number
US05457106

Reaction notes

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