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

HRID 1749357Notes

Reaction equation

HRID 1749357 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]([CH3:25])=[N:17][N:18]([CH3:24])[C:19]=1[CH2:20][CH:21]([CH3:23])[CH3:22]>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]([CH3:25])=[N:17][N:18]([CH3:24])[C:19]=2[CH2:20][CH:21]([CH3:23])[CH3:22])(=[O:11])=[O:10])=[C:4]([Cl:13])[CH:3]=1

Participants

4

Reactant 2

HCID 27374664-Bromo-2,6-dichlorobenzene-1-sulfonyl chlorideHCID 835293184-amino-1,3-dimethyl-5-isobutyl-1H-pyrazole

Product 1

HCID 585613834-Bromo-2,6-dichloro-N-(5-isobutyl-1,3-dimethyl-1H-pyrazol-4-yl)-benzenesulfonamideYield 24%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Prepared from 4-bromo-2,6-dichlorobenzenesulfonyl chloride (0.35 g, 1.1 mmol) and 4-amino-1,3-dimethyl-5-isobutyl-1H-pyrazole (0.18 g, 1.1 mmol) in pyridine (4 ml) according to the method of intermediate 1, to give the title compound as an orange solid (118 mg, 0.26 mmol, 24%). δH (D-6 DMSO, 300K) 7.67 (2H, s), 6.69 (1H, s), 3.71 (3H, s), 2.45 (2H, d J 7.8 Hz), 1.90 (1H, m), 1.84 (3H, s), 0.91 (6H, d J 6.8 Hz). m/z (ES+, 70V) 456.0 (MH+).

Sources & evidence

ORD record
ord-bec049d75fd4476f836430225c340852
Source dataset
uspto-grants-2015_10
Patent number
US09156811B2

Reaction notes

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