4-Bromo-3-methylisoxazol-5-amine → N-(4-Bromo-3-methyl-5-isoxazolyl)-5-(4-ethylphenyl)thiophene-2-sulfonamide

HRID 2270594Notes

Reaction equation

HRID 2270594 reaction equation
Cl[S:2]([C:5]1[S:9][C:8]([C:10]2[CH:15]=[CH:14][C:13]([CH2:16][CH3:17])=[CH:12][CH:11]=2)=[CH:7][CH:6]=1)(=[O:4])=[O:3].[NH2:18][C:19]1[O:23][N:22]=[C:21]([CH3:24])[C:20]=1[Br:25]>CO.C(Cl)(Cl)Cl>[Br:25][C:20]1[C:21]([CH3:24])=[N:22][O:23][C:19]=1[NH:18][S:2]([C:5]1[S:9][C:8]([C:10]2[CH:15]=[CH:14][C:13]([CH2:16][CH3:17])=[CH:12][CH:11]=2)=[CH:7][CH:6]=1)(=[O:4])=[O:3]

Participants

4

Reactant 2

HCID 104875194-Bromo-3-methylisoxazol-5-amineHCID 234455655-Chlorosulphonyl-2-(4-ethylphenyl)thiophene

Product 1

HCID 23445288N-(4-Bromo-3-methyl-5-isoxazolyl)-5-(4-ethylphenyl)thiophene-2-sulfonamide

Reagents, catalysts & solvents 1

HCID 21584188Chloroform methanolSolvent

Procedure

N-(4-bromo-3-methyl-5-isoxazolyl)-5-(4-ethylphenyl) thiophene-2-sulfonamide was prepared in the same manner as described in Example 2. Reaction of 5-chlorosulfonyl-2-(4-ethylphenyl) thiophene (47.1 mg, 0.16 mmol) with 5-amino-4-bromo-3-methyl isoxazole (29 mg, 0.16 mmol) yielded, after flash chromatography using 10% MeOH/CHCl3, a pale brown solid (46 mg, 66% yield), m.p. 172-175° C.

Workup

  1. customyielded

Sources & evidence

ORD record
ord-39c2588cd2bc48818ea37aa01c935fb9
Source dataset
uspto-grants-2001_12
Patent number
US06331637B1

Reaction notes

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