Water → N-(1,1-Dimethylpropyl)-4-bromomethylbenzenesulfonamide

HRID 2258542Notes

Reaction equation

HRID 2258542 reaction equation
[Br:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([S:9](Cl)(=[O:11])=[O:10])=[CH:5][CH:4]=1.C(N(CC)CC)C.[C:20]([NH2:25])([CH2:23][CH3:24])([CH3:22])[CH3:21].O>C1(C)C=CC=CC=1>[CH3:21][C:20]([NH:25][S:9]([C:6]1[CH:7]=[CH:8][C:3]([CH2:2][Br:1])=[CH:4][CH:5]=1)(=[O:11])=[O:10])([CH3:22])[CH2:23][CH3:24]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 689862-Butanamine, 2-methyl-HCID 27344094-(Bromomethyl)benzenesulfonyl chloride

Product 1

HCID 22922484N-(1,1-Dimethylpropyl)-4-bromomethylbenzenesulfonamideYield 8.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

To a solution of 10 g of 4-bromomethylbenzenesulfonyl chloride and 10 ml of triethylamine in 50 ml of toluene is added, dropwise at RT, a solution of 3.2 g of tert-amylamine in 10 ml of toluene, and the mixture is left stirring for 3 hours at RT. Water is then added to the reaction mixture and, after separation by settling, the organic phase is washed with water and dried over Na2SO4, and the solvent is evaporated off under vacuum. The residue is chromatographed on silica, eluting with a DCM/heptane mixture (50/50; v/v). 1 g of the expected product is obtained after crystallization from iso ether, mp=100° C.

Workup

  1. customafter separation
  2. washthe organic phase is washed with water
  3. dry with materialdried over Na2SO4
  4. customthe solvent is evaporated off under vacuum
  5. customThe residue is chromatographed on silica
  6. washeluting with a DCM/heptane mixture (50/50; v/v)

Sources & evidence

ORD record
ord-ebf51210f6824c72812e42710e3bf496
Source dataset
uspto-grants-1997_08
Patent number
US05661169

Reaction notes

Loading…