Hydrochloric Acid → N-(4-t-Butylbenzoyl)-4-vinylbenzenesulfonamide

HRID 2392983Notes

Reaction equation

HRID 2392983 reaction equation
[C:1]([C:5]1[CH:25]=[CH:24][C:8]([C:9]([NH:11][S:12]([C:15]2[CH:20]=[CH:19][C:18]([CH2:21][CH2:22]Br)=[CH:17][CH:16]=2)(=[O:14])=[O:13])=[O:10])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].N12CCCN=C1CCCC=C2.Cl>O1CCCC1>[C:1]([C:5]1[CH:25]=[CH:24][C:8]([C:9]([NH:11][S:12]([C:15]2[CH:16]=[CH:17][C:18]([CH:21]=[CH2:22])=[CH:19][CH:20]=2)(=[O:13])=[O:14])=[O:10])=[CH:7][CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 18977847N-(4-t-Butylbenzoyl)-4-(2-bromoethyl)benzenesulfonamideHCID 219795291,8-Diazabicyclo(5.4.0)undecen-7-ene

Product 1

HCID 18977848N-(4-t-Butylbenzoyl)-4-vinylbenzenesulfonamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 34.00 g (0.08 mol) of N-(4-t-butylbenzoyl)-4-(2-bromoethyl)benzenesulfonamide, 26.79 g (0.176 mol) of 1,8-diazabicyclo[5.4.0]undecen-7-ene (DBU) and 300 ml of tetrahydrofuran was stirred at room temperature for 22 hrs. The reaction mixture was poured into dilute HCl and extracted with methylene chloride twice. The combined extracts were washed twice with water, dried over magnesium sulfate and concentrated. The residue was recrystallized from toluene, collected, washed with toluene and ligroine and dried.

Workup

  1. extractionextracted with methylene chloride twice
  2. washThe combined extracts were washed twice with water
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated
  5. customThe residue was recrystallized from toluene
  6. customcollected
  7. washwashed with toluene and ligroine
  8. customdried

Sources & evidence

ORD record
ord-eb30b8389e1e44508f20332d2245b52a
Source dataset
uspto-grants-1998_09
Patent number
US05804348

Reaction notes

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