1-Chloro-2-nitrobenzene → Benzenesulfonyl chloride, 4-chloro-3-nitro-

HRID 1703736Notes

Reaction equation

HRID 1703736 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[Cl:10])([O-:3])=[O:2].[Cl:11][S:12](O)(=[O:14])=[O:13]>>[N+:1]([C:4]1[CH:9]=[C:8]([S:12]([Cl:11])(=[O:14])=[O:13])[CH:7]=[CH:6][C:5]=1[Cl:10])([O-:3])=[O:2]

Participants

3

Reactant 2

HCID 69451-Chloro-2-nitrobenzeneHCID 24638Chlorosulfonic acid

Product 1

HCID 7323Benzenesulfonyl chloride, 4-chloro-3-nitro-

Procedure

On the other hand, those compounds of formula (1) wherein X is hydroxy and A is a sulfonamido group can be prepared by treating, for example, ortho-nitro-chlorobenzene with chlorosulfonic acid to obtain 3-nitro-4-chlorobenzenesulfonylchloride, followed by treatment with a primary or secondary amine to yield the corresponding 3-nitro-4-chlorobenzene sulfonamido derivative. This product is then treated with caustic soda to yield the 3-nitro-4-hydroxybenzene sulfonamide and subsequently reduced to the desired 3-amino-4-hydroxybenzene sulfonamide.

Workup

  1. customcan be prepared

Sources & evidence

ORD record
ord-efbcd231dfc544c690ced9941717a8a9
Source dataset
uspto-grants-1978_11
Patent number
US04125368

Reaction notes

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