4-Bromo-2,6-dichlorobenzene-1-sulfonyl chloride → 4-Bromo-2,6-dichloro-N-(3-isobutyl-1,5-dimethyl-1H-pyrazol-4-yl)-benzenesulfonamide

HRID 1749356Notes

Reaction equation

HRID 1749356 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([S:9](Cl)(=[O:11])=[O:10])=[C:4]([Cl:13])[CH:3]=1.[NH2:14][C:15]1[C:16]([CH2:22][CH:23]([CH3:25])[CH3:24])=[N:17][N:18]([CH3:21])[C:19]=1[CH3:20]>N1C=CC=CC=1>[Br:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([S:9]([NH:14][C:15]2[C:16]([CH2:22][CH:23]([CH3:25])[CH3:24])=[N:17][N:18]([CH3:21])[C:19]=2[CH3:20])(=[O:11])=[O:10])=[C:4]([Cl:13])[CH:3]=1

Participants

4

Reactant 2

HCID 27374664-Bromo-2,6-dichlorobenzene-1-sulfonyl chlorideHCID 671905434-amino-1,5-dimethyl-3-isobutyl-1H-pyrazole

Product 1

HCID 585612404-Bromo-2,6-dichloro-N-(3-isobutyl-1,5-dimethyl-1H-pyrazol-4-yl)-benzenesulfonamideYield 12.4%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Prepared from 4-bromo-2,6-dichlorobenzenesulfonyl chloride (0.68 g, 2.1 mmol) and 4-amino-1,5-dimethyl-3-isobutyl-1H-pyrazole (0.35 g, 2.1 mmol) in pyridine (5 ml) according to the method of intermediate 1, to give the title compound as a white solid (120 mg, 0.26 mmol, 12%). δH (D-6 DMSO, 300K) 7.65 (2H, s), 6.54 (1H, s), 3.70 (3H, s), 2.17 (3H, s), 1.96 (2H, d J 7.9 Hz), 1.74 (1H, m), 0.78 (6H, d J 6.6 Hz). m/z (ES+, 70V) 456.0 (MH+).

Sources & evidence

ORD record
ord-9e2a8bd7310948208a0c8c3fa505b678
Source dataset
uspto-grants-2015_10
Patent number
US09156811B2

Reaction notes

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