(1,1'-Biphenyl)-4-sulphonyl chloride → N-(3,4-Dimethyl-1,2-oxazol-5-yl)[1,1'-biphenyl]-4-sulfonamide

HRID 1167004Notes

Reaction equation

HRID 1167004 reaction equation
[C:1]1([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:6]=[CH:5][C:4]([S:7](Cl)(=[O:9])=[O:8])=[CH:3][CH:2]=1.[NH2:17][C:18]1[O:22][N:21]=[C:20]([CH3:23])[C:19]=1[CH3:24]>CN(C)C1C=CN=CC=1.N1C=CC=CC=1>[CH3:23][C:20]1[C:19]([CH3:24])=[C:18]([NH:17][S:7]([C:4]2[CH:5]=[CH:6][C:1]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[CH:2][CH:3]=2)(=[O:9])=[O:8])[O:22][N:21]=1

Participants

5

Reactant 2

HCID 74192(1,1'-Biphenyl)-4-sulphonyl chlorideHCID 883175-Amino-3,4-dimethylisoxazole

Product 1

HCID 15453170N-(3,4-Dimethyl-1,2-oxazol-5-yl)[1,1'-biphenyl]-4-sulfonamideYield 45%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

The 4-biphenylsulfonyl chloride from step (a) was added to a solution of 5-amino-3,4-dimethylisoxazole (250 mg, 2.2 mmol) and 4-(dimethyl)aminopyridine (5 mg) in dry pyridine (2.0 ml). The reaction mixture was stirred at room temperature for 4 h. Pyridine was removed under reduced pressure and the residue was partitioned between water and ethyl acetate. The organic layer was washed with 1 N HCl (2×25 ml), brine (25 ml) and dried over anhydrous magnesium sulfate. Evaporation of the solvents left an oily residue that, after purification by column chromatography over silica gel (1% methanol in chloroform as eluent), yielded 337 mg (45%) of a white solid. Recrystallization from ethyl acetate/hexanes gave white crystals, m.p. 154-155° C.

Workup

  1. customPyridine was removed under reduced pressure
  2. customthe residue was partitioned between water and ethyl acetate
  3. washThe organic layer was washed with 1 N HCl (2×25 ml), brine (25 ml)
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customEvaporation of the solvents
  6. waitleft an oily residue that,
  7. customafter purification by column chromatography over silica gel (1% methanol in chloroform as eluent)

Sources & evidence

ORD record
ord-2adbf3fd66bb41be94f67a5aac8ca703
Source dataset
uspto-grants-2003_09
Patent number
US06613804B2

Reaction notes

Loading…