1,8-Diazabicyclo(5.4.0)undec-7-ene → N-(4'-bromo-[1,1'-biphenyl]-2-yl)propane-2-sulfonamide

HRID 1865044Notes

Reaction equation

HRID 1865044 reaction equation
C1CCN2C(=NCCC2)CC1.[Br:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[NH2:25])=[CH:15][CH:14]=1.[CH:26]([S:29](Cl)(=[O:31])=[O:30])([CH3:28])[CH3:27]>C(Cl)Cl>[Br:12][C:13]1[CH:14]=[CH:15][C:16]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[NH:25][S:29]([CH:26]([CH3:28])[CH3:27])(=[O:31])=[O:30])=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 824082-Propanesulfonyl chlorideHCID 113686332-(4'-Bromophenyl)aniline

Product 1

HCID 57974945N-(4'-bromo-[1,1'-biphenyl]-2-yl)propane-2-sulfonamideYield 98%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Add DBU drop wise (8.76 mL, 56.92 mmol) to a solution of 2-(4-bromophenyl)phenylamine (3.53 g, 14.23 mmol) in methylene chloride (50 ml) at 0° C., followed by isopropylsulfonyl chloride (3.29 mL, 28.46 mmol) also added drop wise and stir the reaction at room temperature for 24 h. Remove solvent under reduce pressure and purify the residue by silica gel chromatography eluting with ethyl acetate:hexane 1:4 to ethyl acetate to provide the title compound (4.93 g, 98%). Mass spectrum (m/e): 355 (M+1); 353 (M−1).

Workup

  1. customthe reaction at room temperature for 24 h
  2. custompurify the residue by silica gel chromatography
  3. washeluting with ethyl acetate:hexane 1:4 to ethyl acetate

Sources & evidence

ORD record
ord-21a004d5c96441b6bba2c61bc6b4e822
Source dataset
uspto-grants-2009_12
Patent number
US07625932B2

Reaction notes

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