Hydrochloric Acid → 2-[2-(Methanesulfonyloxy)ethyl]-3-methyl-1-(benzenesulfonyl)indole

HRID 1657322Notes

Reaction equation

HRID 1657322 reaction equation
[CH3:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]([S:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)(=[O:13])=[O:12])[C:3]=1[CH2:20][CH2:21][OH:22].C(N(CC)CC)C.[CH3:30][S:31](Cl)(=[O:33])=[O:32].Cl>ClCCl.O>[CH3:30][S:31]([O:22][CH2:21][CH2:20][C:3]1[N:4]([S:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)(=[O:13])=[O:12])[C:5]2[C:10]([C:2]=1[CH3:1])=[CH:9][CH:8]=[CH:7][CH:6]=2)(=[O:33])=[O:32]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 103136112-[3-Methyl-1-(phenylsulfonyl)indol-2-yl]ethanol

Product 1

HCID 100235022-[2-(Methanesulfonyloxy)ethyl]-3-methyl-1-(benzenesulfonyl)indoleYield 99.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 2-[3-methyl-1-[benzenesulfonyl)indol-2-yl]ethanol (7.1 g) and triethylamine (2.96 g) in dichloromethane (71 ml) was added dropwise methanesulfonyl chloride (2.84 g) in dichloromethane (57 ml) at -40° C. After being stirred at the same temperature for 30 minutes, the reaction mixture was diluted with chilled water, and neutralized with 1N-hydrochloric acid. The organic layer was washed with water, dried over anhydrous magnesium sulfate, and evaporated in vacuo to give 2-[2-(methanesulfonyloxy)ethyl]-3-methyl-1-(benzenesulfonyl)indole (8.8 g) as amorphous powder.

Workup

  1. washThe organic layer was washed with water
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customevaporated in vacuo

Sources & evidence

ORD record
ord-bd299e0f5e114d258f82b45f1ff45365
Source dataset
uspto-grants-1993_10
Patent number
US05256780

Reaction notes

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