Hydrochloric Acid → HCID 90313704, compound

HRID 1524140Notes

Reaction equation

HRID 1524140 reaction equation
B.C1COCC1.[Br:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[S:14]([C:17]([CH3:21])([CH3:20])[C:18]#[N:19])(=[O:16])=[O:15].Cl.[OH-].[Na+]>C1COCC1.O>[Br:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[S:14]([C:17]([CH3:21])([CH3:20])[CH2:18][NH2:19])(=[O:16])=[O:15]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 2723981Borane;tetrahydrofuranHCID 60987889HCID 60987889, compound

Product 1

HCID 90313704HCID 90313704, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

BH3.THF (4 mL, 1 M in THF) was added drop-wise to a solution of 2-((2-bromophenyl)sulfonyl)-2-methylpropanenitrile (258 mg, 1.00 mmol) in THF (1 mL) at rt. The mixture was refluxed for 4 hours and then cooled to rt. Aqueous HCl (5 mL, 6 N) was added and stirring continued for an additional 1 hour. The mixture was basified to pH=9 by addition of NaOH (6 N), diluted with water (20 mL), and extracted with DCM (3×20 mL). The combined extracts were washed with water (2×30 mL) and brine (60 mL), dried over Na2SO4, filtered, and concentrated to dryness to give the crude title compound (203 mg, 70%), which was used in the subsequent step without further purification. MS (ESI): mass calcd. for C10H14NO2S, 290.99; m/z found, 292.1 [M+H]+.

Workup

  1. temperatureThe mixture was refluxed for 4 hours
  2. extractionextracted with DCM (3×20 mL)
  3. washThe combined extracts were washed with water (2×30 mL) and brine (60 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-ba1923b586a245e98cd50f92384c8c26
Source dataset
uspto-grants-2015_07
Patent number
US09079866B2

Reaction notes

Loading…