Triethylamine → HCID 22116059, compound

HRID 1885632Notes

Reaction equation

HRID 1885632 reaction equation
[OH:1][CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH2:15][CH:14]([CH2:16][O:17][C:18]3[CH:27]=[CH:26][C:21]([C:22]([O:24][CH3:25])=[O:23])=[CH:20][CH:19]=3)[CH2:13][C:12]2=[O:28])=[CH:7][CH:6]=1.[CH3:29][S:30](Cl)(=[O:32])=[O:31].C(N(CC)CC)C>C(Cl)Cl>[CH3:29][S:30]([O:1][CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH2:15][CH:14]([CH2:16][O:17][C:18]3[CH:19]=[CH:20][C:21]([C:22]([O:24][CH3:25])=[O:23])=[CH:26][CH:27]=3)[CH2:13][C:12]2=[O:28])=[CH:7][CH:6]=1)(=[O:32])=[O:31]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 22115917HCID 22115917, compound

Product 1

HCID 22116059HCID 22116059, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methyl 4-[1-[4-(2-hydroxyethoxy)phenyl]-2-pyrrolidon-4-yl]methoxybenzoate (3.00 g) is dissolved in methylene chloride (30 ml) and the mixture is cooled with ice. Thereto are added methanesulfonyl chloride (0.90 ml) and triethylamine (2.16 ml) severally and the mixture is stirred at room temperature for 16 hours. The reaction mixture is concentrated under reduced pressure and ethyl acetate (60 ml) is added to the residue. The mixture is washed with water three times, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue is subjected to silica gel column chromatography and eluted with chloroform to give the desired product (3.39 g) as powder.

Workup

  1. temperaturethe mixture is cooled with ice
  2. concentrationThe reaction mixture is concentrated under reduced pressure and ethyl acetate (60 ml)
  3. additionis added to the residue
  4. washThe mixture is washed with water three times
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. washeluted with chloroform

Sources & evidence

ORD record
ord-53b8d54821c34dc0ab438c46c2f87460
Source dataset
uspto-grants-1992_09
Patent number
US05145865

Reaction notes

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