4-Fluorobenzenesulfonyl chloride → 4-fluoro-N-[4-(thiazol-2-yl)benzyl]benzenesulfonamide

HRID 2359819Notes

Reaction equation

HRID 2359819 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8](Cl)(=[O:10])=[O:9])=[CH:4][CH:3]=1.Cl.[S:13]1[CH:17]=[CH:16][N:15]=[C:14]1[C:18]1[CH:25]=[CH:24][C:21]([CH2:22][NH2:23])=[CH:20][CH:19]=1.Cl.C1(C2N=NC(CN)=CC=2)C=CC=CC=1>>[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:23][CH2:22][C:21]2[CH:20]=[CH:19][C:18]([C:14]3[S:13][CH:17]=[CH:16][N:15]=3)=[CH:25][CH:24]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 95884-Fluorobenzenesulfonyl chlorideHCID 51138530(4-(Thiazol-2-yl)phenyl)methanamine hydrochlorideHCID 66717660(6-Phenylpyridazin-3-ylmethyl)amine hydrochloride

Product 1

HCID 547739584-fluoro-N-[4-(thiazol-2-yl)benzyl]benzenesulfonamideYield 85.5%

Procedure

Reaction and post-treatment were carried out in the same manner as in Reference Example 2-(d) except for using 4-fluorobenzenesulfonyl chloride (278 mg, 1.42 mmol) in place of 3-pyridylsulfonyl chloride, and using 4-(thiazol-2-yl)benzylamine hydrochloride (364 mg, 1.38 mmol) obtained in Reference Example 4-(d) in place of (6-phenylpyridazin-3-ylmethyl)amine hydrochloride to afford the title compound (411 mg) as a slightly yellow solid. (Yield: 85%)

Workup

  1. customReaction

Sources & evidence

ORD record
ord-b716730e6ade4ebc9407c306c8ccdb52
Source dataset
uspto-grants-2014_04
Patent number
US08685986B2

Reaction notes

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