5-Amino-3,4-dimethylisoxazole → HCID 23372909, compound

HRID 1899681Notes

Reaction equation

HRID 1899681 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([S:11](Cl)(=[O:13])=[O:12])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[NH2:15][C:16]1[O:20][N:19]=[C:18]([CH3:21])[C:17]=1[CH3:22]>CN(C)C1C=CN=CC=1.N1C=CC=CC=1>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([NH:15][C:16]2[O:20][N:19]=[C:18]([CH3:21])[C:17]=2[CH3:22])(=[O:13])=[O:12])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 883175-Amino-3,4-dimethylisoxazoleHCID 1398824-t-Butylbenzenesulfonyl chloride

Product 1

HCID 23372909HCID 23372909, compoundYield 58.3%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

4-Tert-butylbenzenesulfonyl chloride (498 mg, 2.14 mmol) and 4-(dimethyl)aminopyridine (5 mg) were added to a solution of 5-amino-3,4-dimethylisoxazole (200 mg, 1.78 mmol) 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 which, after purification by column chromatography over silica gel (1% methanol in chloroform as eluent), yielded 320 mg (58%) of an off-white solid. Further purification was achieved by recrystallization from ethyl acetate/hexanes, to yield the pure product as a white solid, m.p. 151°-154° 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 which
  7. customafter purification by column chromatography over silica gel (1% methanol in chloroform as eluent)

Sources & evidence

ORD record
ord-c2b424383d2e4a7cb6e63d44a7859401
Source dataset
uspto-grants-1996_11
Patent number
US05571821

Reaction notes

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