HCID 86692717, compound → HCID 70226032, compound

HRID 1484601Notes

Reaction equation

HRID 1484601 reaction equation
[S:1]([C:5]1[CH:23]=[CH:22][C:8]([O:9][CH2:10][CH2:11][CH2:12][CH2:13][NH:14]C(=O)OC(C)(C)C)=[CH:7][CH:6]=1)(=[O:4])(=[O:3])[NH2:2]>C(O)(C(F)(F)F)=O.C(Cl)Cl>[NH2:14][CH2:13][CH2:12][CH2:11][CH2:10][O:9][C:8]1[CH:22]=[CH:23][C:5]([S:1]([NH2:2])(=[O:3])=[O:4])=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 86692717HCID 86692717, compound

Product 1

HCID 70226032HCID 70226032, compoundYield 177.4%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of tert-butyl (4-(4-sulfamoylphenoxy)butyl)carbamate (0.72 g, 2.09 mmol) in TFA (5.0 mL) and DCM (5.0 mL) was stirred at rt for overnight. After the solvent was evaporated under a steam of N2, the reaction mixture was dissolved in water (20.0 mL) and acetonitrile (5.0 mL) and lyophilized to afford 4-(4-aminobutoxy)benzenesulfonamide as a yellow solid (0.906 g) containing TFA. 1H NMR (400 MHz, DMSO) 7.74-7.72 (m, 4H), 7.20 (s, 2H), 7.06 (d, 2H), 4.06 (t, 2H), 2.89-2.82 (m, 2H), 1.80-1.75 (m, 2H), 1.71-1.65 (m, 2H); MS (ESI), 245.1 (M+H)+.

Workup

  1. customAfter the solvent was evaporated under a steam of N2
  2. dissolutionthe reaction mixture was dissolved in water (20.0 mL)

Sources & evidence

ORD record
ord-9def7726d454433ab0885bfa597b47c5
Source dataset
uspto-grants-2016_08
Patent number
US09422251B2

Reaction notes

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