Water → 3-Chloro-4-(2-(2-methoxyethoxy)ethylthio)benzenesulfonamide

HRID 574790Notes

Reaction equation

HRID 574790 reaction equation
[H-].[Na+].[CH3:3][O:4][CH2:5][CH2:6][O:7][CH2:8][CH2:9][SH:10].[Cl:11][C:12]1[CH:13]=[C:14]([S:19]([NH2:22])(=[O:21])=[O:20])[CH:15]=[CH:16][C:17]=1F.O>O1CCCC1>[Cl:11][C:12]1[CH:13]=[C:14]([S:19]([NH2:22])(=[O:20])=[O:21])[CH:15]=[CH:16][C:17]=1[S:10][CH2:9][CH2:8][O:7][CH2:6][CH2:5][O:4][CH3:3]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 75098833-Chloro-4-fluorobenzenesulfonamideHCID 114008022-(2-Methoxyethoxy)ethane-1-thiol

Product 1

HCID 671266643-Chloro-4-(2-(2-methoxyethoxy)ethylthio)benzenesulfonamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
110 °C

Procedure

In a 25 ml, microwave tube was added sodium hydride (0.6 g) in tetrahydrofuran (10 mL) to give a suspension. 2-(2-Methoxyethoxy)ethanethiol (1 g) was added slowly. After stirring for 30 minutes, 3-chloro-4-fluorobenzenesulfonamide (1.54 g) dissolved in 10 mL tetrahydrofuran was added slowly. The mixture was heated at 110° C. for 30 minutes in a Biotage Initiator microwave reactor. Water was added, the product was extracted with ether (20 mL×3), dried over Na2SO4, filtered, and the solvent was removed under reduced pressure. The crude product was purified by flash chromatography on silica eluting with 0-25% ethyl acetate in hexane.

Workup

  1. customto give a suspension
  2. additionwas added slowly
  3. extractionthe product was extracted with ether (20 mL×3)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customthe solvent was removed under reduced pressure
  7. customThe crude product was purified by flash chromatography on silica eluting with 0-25% ethyl acetate in hexane

Sources & evidence

ORD record
ord-603cc6ad3e834fe18038eee18d6b3ca2
Source dataset
uspto-grants-2015_05
Patent number
US09034875B2

Reaction notes

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