Benzenesulfonyl chloride → N-benzenesulfonyl-4-(2-bromoethyl) benzenesulfonamide

HRID 1980602Notes

Reaction equation

[Br:1][CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([S:10]([NH2:13])(=[O:12])=[O:11])=[CH:6][CH:5]=1.[C:14]1([S:20](Cl)(=[O:22])=[O:21])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[OH-].[Na+]>>[C:14]1([S:20]([NH:13][S:10]([C:7]2[CH:6]=[CH:5][C:4]([CH2:3][CH2:2][Br:1])=[CH:9][CH:8]=2)(=[O:11])=[O:12])(=[O:22])=[O:21])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

Reactant 3

HCID 7369Benzenesulfonyl chloride

HCID 14798Sodium Hydroxide

HCID 144850914-(2-Bromoethyl)benzenesulfonamide

Product 1

HCID 54306985N-benzenesulfonyl-4-(2-bromoethyl) benzenesulfonamide

Procedure

As an additional variation of the reaction sequence, the 4-(2-bromoethyl) benzenesulfonamide produced as in Example I was reacted with benzenesulfonyl chloride and sodium hydroxide and then acidified to produce N-benzenesulfonyl-4-(2-bromoethyl) benzenesulfonamide. Recrystallization of a small portion from toluene gave a white solid, having a melting point of 148°-150° C. and a neutralization equivalent of 405 (theory 404).

Sources & evidence

ORD record: ord-f192f9618b0c45879ad30df35d6ed0ae
Source dataset: uspto-grants-1985_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04510324

Reaction notes

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