Hydrochloric Acid → N-(4-vinylbenzoyl)-4-methoxybenzenesulfonamide

HRID 363281

Reaction equation

HRID 363281 reaction equation
Br[CH2:2][CH2:3][C:4]1[CH:23]=[CH:22][C:7]([C:8]([NH:10][S:11]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)(=[O:13])=[O:12])=[O:9])=[CH:6][CH:5]=1.N12CCCN=C1CCCCC2.Cl>C1COCC1>[CH:3]([C:4]1[CH:23]=[CH:22][C:7]([C:8]([NH:10][S:11]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)(=[O:13])=[O:12])=[O:9])=[CH:6][CH:5]=1)=[CH2:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 67587147N-[4-(2-bromoethyl)benzoyl]-4-methoxybenzenesulfonamide

Product 1

HCID 15404407N-(4-vinylbenzoyl)-4-methoxybenzenesulfonamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 35.85 g (0.09 mol) of N-[4-(2-bromoethyl)benzoyl]-4-methoxybenzenesulfonamide, 27.40 g (0.18 mol) of 1,8-diazabicyclo-[5.4.0]undec-7-ene (DBU) and 375 ml of THF was stirred at room temperature for 19.5 hrs. Solid formed within 30 mins. The mixture was poured into dilute HCl giving an oily precipitate which crystallized. The solid was collected, washed with water, redissolved in methylene chloride, dried over magnesium sulfate and concentrated to an oil which crystallized. The solid was collected, recrystallized from toluene, collected, washed with ligroine and dried.

Workup

  1. customSolid formed within 30 mins
  2. customcrystallized
  3. customThe solid was collected
  4. washwashed with water
  5. dissolutionredissolved in methylene chloride
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated to an oil which
  8. customcrystallized
  9. customThe solid was collected
  10. customrecrystallized from toluene
  11. customcollected
  12. washwashed with ligroine
  13. customdried

Sources & evidence

ORD record
ord-cbd759d9c45c482fbeab048a3d68cc39
Source dataset
uspto-grants-1999_02
Patent number
US05874194

Linked notes

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