2-Nitrobenzenesulfonyl chloride → HCID 10709109, compound

HRID 439406Notes

Reaction equation

HRID 439406 reaction equation
[CH3:1][C:2]1[C:6]([CH3:7])=[C:5]([NH2:8])[O:4][N:3]=1.[N+:9]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[S:18](Cl)(=[O:20])=[O:19])([O-:11])=[O:10]>N1C=CC=CC=1>[CH3:1][C:2]1[C:6]([CH3:7])=[C:5]([NH:8][S:18]([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[N+:9]([O-:11])=[O:10])(=[O:19])=[O:20])[O:4][N:3]=1

Participants

4

Reactant 2

HCID 155402-Nitrobenzenesulfonyl chlorideHCID 883175-Amino-3,4-dimethylisoxazole

Product 1

HCID 10709109HCID 10709109, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 4.04 g (36 mmol) of 3,4-dimethyl-5-isoxazolamine in 15 mL of pyridine, 8.0 g (36 mmol) of 2-nitrobenzenesulfonyl chloride was added and the solution was stirred at room temperature overnight. The mixture was poured into 100 mL of ice water and filtered. The filtrate was acidified to pH 2 using 6N aqueous hydrochloric acid and the mixture was extracted with 4×125 mL of ethyl acetate. The combined organic extracts were washed with 75 mL of brine, dried and evaporated to provide 9.1 g of a dark brown residue. This material was chromatographed on silica gel using hexanes/ethyl acetate (2:1) to provide 0.5 g of Example 9 as a light yellow solid. Melting point: 91°-94° C. Analysis for C11H11N3O5S Calc'd: C, 44.44; H, 3.73; N, 14.13; S, 10.78. Found: C, 44.75; H, 3.69; N, 14.01; S, 11.06.

Workup

  1. filtrationfiltered
  2. extractionthe mixture was extracted with 4×125 mL of ethyl acetate
  3. washThe combined organic extracts were washed with 75 mL of brine
  4. customdried
  5. customevaporated

Sources & evidence

ORD record
ord-b6e3a46f5ea64446a1191212fddbf8b3
Source dataset
uspto-grants-1996_05
Patent number
US05514696

Reaction notes

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