4-Methoxybenzenesulfonamide → N-[4-(2-bromoethyl)benzoyl]-4-methoxybenzenesulfonamide

HRID 363280

Reaction equation

HRID 363280 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([NH2:12])(=[O:11])=[O:10])=[CH:5][CH:4]=1.[Br:13][CH2:14][CH2:15][C:16]1[CH:24]=[CH:23][C:19]([C:20](Cl)=[O:21])=[CH:18][CH:17]=1>C1(C)C=CC=CC=1>[Br:13][CH2:14][CH2:15][C:16]1[CH:24]=[CH:23][C:19]([C:20]([NH:12][S:9]([C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=2)(=[O:11])=[O:10])=[O:21])=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 707894-MethoxybenzenesulfonamideHCID 140920984-(2-Bromoethyl)benzoyl chloride

Product 1

HCID 67587147N-[4-(2-bromoethyl)benzoyl]-4-methoxybenzenesulfonamide

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 18.72 g (0.10 mol) of 4-methoxybenzenesulfonamide, 24.75 g (0.10 mol) of 4-(2-bromoethyl)benzoyl chloride and 200 ml of toluene was stirred and heated to reflux at which time solution was achieved. The solution was heated at reflux for 16.5 hrs. The vapors emitted from the condenser were acidic during reaction. After this time, the solution was cooled and concentrated to an oil. The oil was dissolved in 3:7 heptane:toluene and cooled. Solid crystallized and was collected, washed with ligroine and dried.

Workup

  1. temperatureheated
  2. temperatureto reflux at which time solution
  3. temperatureThe solution was heated
  4. temperatureat reflux for 16.5 hrs
  5. customwere acidic during reaction
  6. temperatureAfter this time, the solution was cooled
  7. concentrationconcentrated to an oil
  8. dissolutionThe oil was dissolved in 3:7 heptane
  9. temperaturetoluene and cooled
  10. customSolid crystallized
  11. customwas collected
  12. washwashed with ligroine
  13. customdried

Sources & evidence

ORD record
ord-9502383a01704f438e73efde5cc03129
Source dataset
uspto-grants-1999_02
Patent number
US05874194

Linked notes

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