p-Bromobenzenesulfonyl chloride → 4-bromo-N-(2-hydroxyethyl)-N-methylbenzenesulfonamide

HRID 70558Notes

Reaction equation

HRID 70558 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8](Cl)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[CH3:12][NH:13][CH2:14][CH2:15][OH:16]>C(Cl)(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:13]([CH2:14][CH2:15][OH:16])[CH3:12])(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 7396p-Bromobenzenesulfonyl chlorideHCID 80162-(Methylamino)ethanol

Product 1

HCID 394031924-bromo-N-(2-hydroxyethyl)-N-methylbenzenesulfonamide

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of 4-bromobenzenesulfonyl chloride (1.10 g) in chloroform (10 mL) was stirred in an ice bath, during which N-methylethanolamine (5 mL) was slowly added dropwise thereto. The mixture was returned to room temperature and stirred for about 2.5 hours. The reaction solution was quenched with concentrated hydrochloric acid with stirring again in an ice bath. The mixed solution was poured into 6 M hydrochloric acid (10 mL) as such, followed by extraction with chloroform. The organic layer was dried over anhydrous magnesium sulfate and filtered, after which the filtrate was concentrated under reduced pressure to give a crude product of 4-bromo-N-(2-hydroxyethyl)-N-methylbenzenesulfonamide as a colorless oil (1.339 g, quant.).

Workup

  1. additionwas slowly added dropwise
  2. customwas returned to room temperature
  3. customThe reaction solution was quenched with concentrated hydrochloric acid
  4. stirringwith stirring again in an ice bath
  5. additionThe mixed solution was poured into 6 M hydrochloric acid (10 mL) as such,
  6. extractionfollowed by extraction with chloroform
  7. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. concentrationafter which the filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-72b90cee6b8d4917905f3a688a617b53
Source dataset
uspto-grants-2014_09
Patent number
US08822503B2

Reaction notes

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