4-Methoxybenzenesulfonyl chloride → HCID 22711751, compound

HRID 352397Notes

Reaction equation

HRID 352397 reaction equation
[NH2:1][C:2]([CH3:6])([CH3:5])[CH2:3][OH:4].C(N(CC)CC)C.[CH3:14][O:15][C:16]1[CH:21]=[CH:20][C:19]([S:22](Cl)(=[O:24])=[O:23])=[CH:18][CH:17]=1>C1COCC1.O>[OH:4][CH2:3][C:2]([NH:1][S:22]([C:19]1[CH:18]=[CH:17][C:16]([O:15][CH3:14])=[CH:21][CH:20]=1)(=[O:24])=[O:23])([CH3:6])[CH3:5]

Participants

6

Reactant 3

HCID 74014-Methoxybenzenesulfonyl chlorideHCID 8471TriethylamineHCID 118072-Amino-2-methyl-1-propanol

Product 1

HCID 22711751HCID 22711751, compoundYield 79.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Part A: To a solution of 4.47 g (50 mmol) of 2-amino-2-methyl-1-propanol in 20 mL of THF and 5 mL of water, was added 10 mL (72 mmol) of triethylamine. After cooling in an ice bath, 9.0 g (44 mmol) of 4-methoxybenzenesulfonyl chloride was slowly added over 10 minutes. After stirring at room temperature for 12 hours, the reaction was concentrated, ethyl acetate and water were added, the organic layer was separated and washed with 5% potassium hydrogen sulfate solution, saturated sodium bicarbonate solution and brine, dried over sodium sulfate, filtered and concentrated to afford 9.1 g of the desired N-(2-hydroxy-1,1-dimethylethyl)-4-methoxybenzenesulfonamide.

Workup

  1. temperatureAfter cooling in an ice bath
  2. concentrationthe reaction was concentrated
  3. additionethyl acetate and water were added
  4. customthe organic layer was separated
  5. washwashed with 5% potassium hydrogen sulfate solution, saturated sodium bicarbonate solution and brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-bddfbcd05b854ae8ad832743ae99352d
Source dataset
uspto-grants-2004_06
Patent number
US06747027B1

Reaction notes

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