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

HRID 378422Notes

Reaction equation

HRID 378422 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 1N 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 1N 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-2297f2a8ec3d4bd79476e70db82a3559
Source dataset
uspto-grants-2000_02
Patent number
US06030991

Reaction notes

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