Hydrochloric Acid → 3-bromo-N-(2-hydroxy-1,1-dimethylethyl)benzenesulfonamide

HRID 1989261Notes

Reaction equation

HRID 1989261 reaction equation
[NH2:1][C:2]([CH3:6])([CH3:5])[CH2:3][OH:4].[Br:7][C:8]1[CH:9]=[C:10]([S:14](Cl)(=[O:16])=[O:15])[CH:11]=[CH:12][CH:13]=1.Cl>O1CCOCC1.CCOC(C)=O>[Br:7][C:8]1[CH:9]=[C:10]([S:14]([NH:1][C:2]([CH3:6])([CH3:5])[CH2:3][OH:4])(=[O:16])=[O:15])[CH:11]=[CH:12][CH:13]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 118072-Amino-2-methyl-1-propanolHCID 17943m-Bromobenzenesulphonyl chloride

Product 1

HCID 435019003-bromo-N-(2-hydroxy-1,1-dimethylethyl)benzenesulfonamide

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
23 °C

Procedure

To a solution of commercially available 2-amino-2-methyl-1-propanol (8.91 g, 100 mmol) in dioxane (20 mL) at 5° C. was added commercially available 3-bromobenzenesulfonyl chloride (2.88 mL, 20 mmol) and the mixture was vigorously stirred at 23° C. for 1 h. Poured into 1 N HCl, diluted with EtOAc, separated phases, washed organic layer with brine, dried over Na2SO4. Removal of the solvent in vacuum left the title compound as a white solid (5.47 g, 89%). MS (ISN) 306.1 [(M−H)−] and 308.2 [(M+2−H)−]; mp 138° C.

Workup

  1. customseparated phases
  2. washwashed organic layer with brine
  3. dry with materialdried over Na2SO4
  4. customRemoval of the solvent in vacuum
  5. waitleft the title compound as a white solid (5.47 g, 89%)

Sources & evidence

ORD record
ord-f4b35dd1b9c34a29bbfdf4671d03cf3f
Source dataset
uspto-grants-2010_01
Patent number
US07642264B2

Reaction notes

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