Benzenesulfonyl chloride, 3,4-dichloro- → HCID 57678944, compound

HRID 491859Notes

Reaction equation

HRID 491859 reaction equation
[CH3:1][O:2][C:3](=[O:17])[CH2:4][S:5][C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([O:15][CH3:16])[CH:13]=2)[NH:8][CH:7]=1.[OH-].[K+].[Cl:20][C:21]1[CH:22]=[C:23]([S:28](Cl)(=[O:30])=[O:29])[CH:24]=[CH:25][C:26]=1[Cl:27]>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.C(Cl)Cl>[CH3:1][O:2][C:3](=[O:17])[CH2:4][S:5][C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([O:15][CH3:16])[CH:13]=2)[N:8]([S:28]([C:23]2[CH:24]=[CH:25][C:26]([Cl:27])=[C:21]([Cl:20])[CH:22]=2)(=[O:30])=[O:29])[CH:7]=1

Participants

6

Reactant 3

HCID 7383Benzenesulfonyl chloride, 3,4-dichloro-HCID 14797Potassium HydroxideHCID 57678947HCID 57678947, compound

Product 1

HCID 57678944HCID 57678944, compound

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 6344DichloromethaneSolvent

Procedure

To a dry round bottom flask, (5-Methoxy-1H-indol-3-ylsulfanyl)-acetic acid methyl ester (25, 7.0 mg, 0.027 mmol) was dissolved with CH2Cl2 (3.0 mL). Tetrabutylammonium hydrogen sulfate (2.0 mg) and 50% KOH solution (3.0 mL) were added next. After about 5 minutes of stirring, 3,4-dichloro-benzenesulfonyl chloride (20 mg, 0.081 mmol) was added. This reaction was allowed to stir at ambient temperature overnight. The reaction was extracted with dichloromethane (2×14 mL), washed with water (5 mL), brine (5 mL) and dried over anhydrous magnesium sulfate. The reactant was filtered and rotoevaporated to give the desired product 26 as off white solid.

Workup

  1. stirringto stir at ambient temperature overnight
  2. extractionThe reaction was extracted with dichloromethane (2×14 mL)
  3. washwashed with water (5 mL), brine (5 mL)
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationThe reactant was filtered

Sources & evidence

ORD record
ord-46a6736ce26f48cf8f7f00dc55bf1ce6
Source dataset
uspto-grants-2009_05
Patent number
US07531568B2

Reaction notes

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