Potassium Carbonate → HCID 86692718, compound

HRID 2273343Notes

Reaction equation

HRID 2273343 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH2:11])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[C:12]([O:16][C:17](=[O:26])[NH:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]Br)([CH3:15])([CH3:14])[CH3:13].C([O-])([O-])=O.[K+].[K+]>C(#N)C.Cl>[C:12]([O:16][C:17](=[O:26])[NH:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][O:1][C:2]1[CH:7]=[CH:6][C:5]([S:8](=[O:9])(=[O:10])[NH2:11])=[CH:4][CH:3]=1)([CH3:15])([CH3:14])[CH3:13]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 74093p-HydroxybenzenesulfonamideHCID 16211353tert-Butyl (6-bromohexyl)carbamate

Product 1

HCID 86692718HCID 86692718, compoundYield 43%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
75 °C

Procedure

To a solution of 4-hydroxybenzenesulfonamide (1.73 g, 10.0 mmol) and tert-butyl(6-bromohexyl)carbamate (2.1 g, 7.5 mmol) in acetonitrile (50 mL) was added anhydrous K2CO3 (2.07 g, 15 mmol). The reaction mixtures were stirred at 75° C. for overnight. Solvent was evaporated under reduced pressure to give a residue. The residue was diluted with 1 N HCl (40 mL), extracted with DCM, and dried over Na2SO4. Solvent was evaporated under reduce pressure to afford a residue, which was purified by biotage eluting with DCM to 10% MeOH in DCM to afford tert-butyl(6-(4-sulfamoylphenoxy)hexyl)carbamate (1.192 g, 43%).

Workup

  1. customThe reaction mixtures
  2. customSolvent was evaporated under reduced pressure
  3. customto give a residue
  4. extractionextracted with DCM
  5. dry with materialdried over Na2SO4
  6. customSolvent was evaporated
  7. customto afford a residue, which
  8. customwas purified by biotage
  9. washeluting with DCM to 10% MeOH in DCM

Sources & evidence

ORD record
ord-156609320f314f709ea5be5f44baf020
Source dataset
uspto-grants-2015_09
Patent number
US09120837B2

Reaction notes

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