Ammonium Hydroxide → HCID 58275523, compound

HRID 42337Notes

Reaction equation

HRID 42337 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([NH:12][C:13]([CH3:16])([CH3:15])[CH3:14])(=[O:11])=[O:10])=[C:5]([F:17])[CH:4]=1.[NH4+:18].[OH-]>C1COCC1.CO>[NH2:18][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([NH:12][C:13]([CH3:16])([CH3:15])[CH3:14])(=[O:11])=[O:10])=[C:5]([F:17])[CH:4]=1

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 10881860HCID 10881860, compound

Product 1

HCID 58275523HCID 58275523, compound

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a solution of 4-(bromomethyl)-N-tert-butyl-2-fluorobenzenesulfonamide (500 mg) in THF/MeOH (1:1, 15 ml) was added NH4OH (4.5 ml). The mixture was stirred at room temperature overnight. The reaction mixture was concentrated and partitioned between EtOAc/H2O and the aq phase was extracted by EtOAc (3×). The organic phase was then combined, washed with brine, dried over Na2SO4 and concentrated to give 4-(aminomethyl)-N-tert-butyl-2-fluorobenzenesulfonamide as a viscous oil, which was used in the next step without further purification.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. custompartitioned between EtOAc/H2O
  3. extractionthe aq phase was extracted by EtOAc (3×)
  4. washwashed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-c56a1fc7401845a9bd5acdf596b49e7d
Source dataset
uspto-grants-2013_09
Patent number
US08536187B2

Reaction notes

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