Triethylamine → HCID 20400823, compound

HRID 1980863Notes

Reaction equation

HRID 1980863 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[OH:6][CH2:7][CH2:8][C:9]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[NH:11][C:10]=1[C:18]1[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=1.C(N(CC)CC)C>C(Cl)Cl>[CH3:1][S:2]([O:6][CH2:7][CH2:8][C:9]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[NH:11][C:10]=1[C:18]1[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=1)(=[O:4])=[O:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 20400799HCID 20400799, compound

Product 1

HCID 20400823HCID 20400823, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methanesulfonyl chloride (2.50 ml) is added dropwise to a solution of 7.5 g 3-(2-hydroxyethyl)-2-(3-pyridyl)-indole and 10.0 ml of triethylamine in 150 ml of methylene chloride at -10°. This mixture is stirred at room temperature for 0.5 hour and poured into 600 ml of ice water. The resulting slurry is extracted with methylene chloride and the extract is washed with saturated sodium bicarbonate solution, dried over MgSO4 and evaporated in vacuo to give 3-(2-methylsulfonyloxyethyl)-2-(3-pyridyl)-indole.

Workup

  1. extractionThe resulting slurry is extracted with methylene chloride
  2. washthe extract is washed with saturated sodium bicarbonate solution
  3. dry with materialdried over MgSO4
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-7eb58fb0a8764196b39949cdcfc5de31
Source dataset
uspto-grants-1985_04
Patent number
US04511573

Reaction notes

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