Benzenesulfonyl chloride → N-(4-chloro-5-methyl-3-isoxazolyl)benzenesulfonamide

HRID 842893Notes

Reaction equation

HRID 842893 reaction equation
[NH2:1][C:2]1[C:6]([Cl:7])=[C:5]([CH3:8])[O:4][N:3]=1.[C:9]1([S:15](Cl)(=[O:17])=[O:16])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>>[Cl:7][C:6]1[C:2]([NH:1][S:15]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)(=[O:17])=[O:16])=[N:3][O:4][C:5]=1[CH3:8].[NH2:1][C:2]1[C:6]([Cl:7])=[C:5]([CH3:8])[O:4][N:3]=1.[C:9]1([S:15]([N:1]([C:2]2[C:6]([Cl:7])=[C:5]([CH3:8])[O:4][N:3]=2)[S:15]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)(=[O:17])=[O:16])(=[O:17])=[O:16])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

5

Reactant 2

HCID 7369Benzenesulfonyl chlorideHCID 180092614-Chloro-5-methyl-1,2-oxazol-3-amine

Product 3

HCID 180092614-Chloro-5-methyl-1,2-oxazol-3-amineYield 25%HCID 18617386N-(4-chloro-5-methyl-3-isoxazolyl)benzenesulfonamideYield 40%HCID 18617402N-(benzenesulfonyl)-N-(4-chloro-5-methyl-3-isoxazolyl)benzenesulfonamideYield 7%

Procedure

N-(4-chloro-5-methyl-3-isoxazolyl)benzenesulfonamide was prepared from 3-amino-4-chloro-5-methylisoxazole and benzenesulfonyl chloride as described in Example 26b in 40% yield. The crude product was purified by column chromatography with 10-100% ethyl acetate/hexanes as eluent. A crystalline solid was obtained after recrystallization from ethyl acetate/hexanes, m.p. 139-141° C. 3-Amino-4-chloro-5-methylisoxazole (25% recovery) and N-(benzenesulfonyl)-N-(4-chloro-5-methyl-3-isoxazolyl)benzenesulfonamide (7% yield) were also obtained as less polar products.

Workup

  1. customThe crude product was purified by column chromatography with 10-100% ethyl acetate/hexanes as eluent
  2. customA crystalline solid was obtained
  3. customafter recrystallization from ethyl acetate/hexanes, m.p. 139-141° C

Sources & evidence

ORD record
ord-23ba051367474be88fbf2d942bef25f6
Source dataset
uspto-grants-2002_04
Patent number
US06376523B1

Reaction notes

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