Benzene → N-tert-butyl-4'-aminobiphenyl-2-sulfonamide

HRID 2230780Notes

Reaction equation

HRID 2230780 reaction equation
Br[C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.[C:9]([NH:13][S:14]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1B(O)O)(=[O:16])=[O:15])([CH3:12])([CH3:11])[CH3:10].C(=O)([O-])[O-].[Na+].[Na+].C1C=CC=CC=1>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C(Cl)Cl.O.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[NH2:6][C:5]1[CH:7]=[CH:8][C:2]([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=2[S:14]([NH:13][C:9]([CH3:12])([CH3:11])[CH3:10])(=[O:15])=[O:16])=[CH:3][CH:4]=1

Participants

9

Reactant 4

HCID 241BenzeneHCID 78074-BromoanilineHCID 10340Sodium CarbonateHCID 4997616Boronic acid, B-(2-(((1,1-dimethylethyl)amino)sulfonyl)phenyl)-

Product 1

HCID 10804475N-tert-butyl-4'-aminobiphenyl-2-sulfonamideYield 41.4%

Reagents, catalysts & solvents 4

HCID 74236Tetrabutylammonium BromideCatalystHCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 3.44 g (20 mmol) of 4-bromoaniline and 5.14 g (20 mmol) of 2-(t-butylaminosulfonyl)phenylboronic acid, 1.16 g of tetrakis(triphenylphosphine) palladium(0) (1 mmol), 0.32 g of tetrabutylammonium bromide (1 mmol) and 20 mL of 2M aqueous sodium carbonate were refluxed with 180 mL of benzene under N2 for 5.5 hours. After cooling, the mixture was diluted with methylene chloride and water. The two phases were separated and the organic phase was washed with water, dried with MgSO4 and concentrated in vacuo. The resulting thick oil was chromatographed on silica with 30% EtOAc/hexane to afford 2.52 g (41%) of the aniline. 1H NMR (CDCl3): δ8.14 (d, 1H); 7.53 (t, 1H); 7.43 (t, 1H); 7.33 (d, 2H); 7.27 (d, 1H); 6.76 (d, 2H); 3.7 (br s, 1H); 0.99 (s, 9H).

Workup

  1. temperatureAfter cooling
  2. customThe two phases were separated
  3. washthe organic phase was washed with water
  4. dry with materialdried with MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe resulting thick oil was chromatographed on silica with 30% EtOAc/hexane

Sources & evidence

ORD record
ord-98f5422314544719bef3401c90eb3074
Source dataset
uspto-grants-2002_07
Patent number
US06426346B1

Reaction notes

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