Tert-Butylamine → HCID 86760921, compound

HRID 229596Notes

Reaction equation

HRID 229596 reaction equation
C([C:4]1[CH:5]=[CH:6][C:7]([CH2:14][CH2:15][NH:16][C:17](=[O:22])[C:18]([F:21])([F:20])[F:19])=[C:8]([S:10](Cl)(=[O:12])=[O:11])[CH:9]=1)(C)C.[C:23]([NH2:27])([CH3:26])([CH3:25])[CH3:24].O1C[CH2:31][CH2:30][CH2:29]1>>[C:23]([NH:27][S:10]([C:8]1[CH:9]=[CH:4][C:5]([CH:30]([CH3:31])[CH3:29])=[CH:6][C:7]=1[CH2:14][CH2:15][NH:16][C:17](=[O:22])[C:18]([F:19])([F:20])[F:21])(=[O:11])=[O:12])([CH3:26])([CH3:25])[CH3:24]

Participants

4

Reactant 3

HCID 6385Tert-ButylamineHCID 8028TetrahydrofuranHCID 17856313HCID 17856313, compound

Product 1

HCID 86760921HCID 86760921, compound

Procedure

To a solution of 0.463 g of 5-isopropyl-2-[2-(2,2,2-trifluoroacetylamino)ethyl]benzenesulfonyl chloride in 30 mL of tetrahydrofuran was added 0.500 mL of tert-butylamine. The mixture was sealed and stirred at room temperature overnight. The reaction mixture was concentrated under reduced pressure, and the residue was dissolved in 30 mL of water and 10 mL of 1 mol/L hydrochloric acid. The mixture was extracted with ethyl acetate, and the organic layer was washed with water, saturated aqueous sodium bicarbonate solution, and brine. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure to give 0.481 g of N-[2-(2-tert-butylsulfamoyl-5-isopropylphenyl)ethyl]-2,2,2-trifluoroacetamide.

Workup

  1. customThe mixture was sealed
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. dissolutionthe residue was dissolved in 30 mL of water
  4. extractionThe mixture was extracted with ethyl acetate
  5. washthe organic layer was washed with water, saturated aqueous sodium bicarbonate solution, and brine
  6. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  7. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-94e4659f1086489d9d80cf265b400c6e
Source dataset
uspto-grants-2009_07
Patent number
US07563822B2

Reaction notes

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