GB1223619A - 4-hydroxybenzenesulphonyl derivatives, the preparation thereof and compositions containing them - Google Patents

4-hydroxybenzenesulphonyl derivatives, the preparation thereof and compositions containing them

Info

Publication number
GB1223619A
GB1223619A GB4205468A GB4205468A GB1223619A GB 1223619 A GB1223619 A GB 1223619A GB 4205468 A GB4205468 A GB 4205468A GB 4205468 A GB4205468 A GB 4205468A GB 1223619 A GB1223619 A GB 1223619A
Authority
GB
United Kingdom
Prior art keywords
group
general formula
hydrogen atom
atom
hydroxybenzenesulphonyl
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
GB4205468A
Inventor
John Yates
Ernest Haddock
Elliot Bergman
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Shell Internationale Research Maatschappij BV
Original Assignee
Shell Internationale Research Maatschappij BV
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Shell Internationale Research Maatschappij BV filed Critical Shell Internationale Research Maatschappij BV
Priority to GB4205468A priority Critical patent/GB1223619A/en
Publication of GB1223619A publication Critical patent/GB1223619A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
    • C07C309/63—Esters of sulfonic acids
    • C07C309/72—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
    • C07C309/75—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing singly-bound oxygen atoms bound to the carbon skeleton

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

1,223,619. 4 - Hydroxybenzenesulphonyl derivatives. SHELL INTERNATIONALE RESEARCH MAATSCHAPPIJ N.V. 17 July, 1969 [4 Sept., 1968[, No. 42054/68. Heading C2C. [Also in Division A5] Novel 4-hydroxybenzenesulphonyl derivatives of the general formula wherein R 1 is a hydrogen atom, an optionally alkyl-substituted ammonium ion or an acyl group; X is a hydrogen or halogen atom or a nitro group; Y is a halogen atom or an optionally substituted sulphonamido group; and Z is an alkoxy or azido group or a group of the formula NR 2 R 3 in which R 2 is a hydrogen atom or an alkyl group and R 3 is a hydrogen atom or an alkyl, alkoxy, hydroxy, amino or acyl group, or R 2 and R 3 , together with the nitrogen atom to which they are attached, form a saturated heterocyclic ring, with the proviso that when X and Y are both a bromine atom and are located at the 3- and 5-positions of the benzene ring relative to the sulphonyl group and R 1 is a hydrogen atom, then Z is not an amino group, are prepared (a) when R 1 is a hydrogen atom and Z is a group of the formula NR 2 R 3 in which R 3 is not an acyl group, by reaction of a 4- hydroxybenzenesulphonyl halide of the general formula wherein Hal is a halogen atom, with an excess of ammonia or an amine of the general formula R 2 R 3 NH and acidification of the reaction mixture; (b) when R 1 is an optionally alkylsubstituted ammonium ion, by treatment of the corresponding compound of the first general formula above wherein R 1 is a hydrogen atom with ammonia or an amine; (c) when R 1 is a hydrogen atom and Z is an alkoxy or azido group, by treatment of a 4-hydroxybenzenesulphonyl halide of the second general formula above with an alcohol or an alkali metal azide, respectively; (d) when R 1 is an acyl group, by reaction of the corresponding compound of the first general formula above wherein R 1 is a hydrogen atom with an acyl halide of the general formula R 1 Hal, wherein Hal is a halogen atom; (e) when R 1 is an alkylcarbamoyl group, by reaction of the corresponding compound of the first general formula above, wherein R 1 is a hydrogen atom with an alkyl isocyanate; (f) when Z is an acyl-substituted amino group, by heating under reflux the corresponding compound of the first general formula above wherein Z is an amino group and an acyl halide of the fourth general formula above; (g) when X and Y are both an iodine atom and R 1 is a hydrogen atom, by heating a 4-hydroxybenzenesulphonyl derivative of the general formula with an excess of iodine chloride; and (h) when Y is a sulphonamido group and R 1 is a hydrogen atom, by reaction of a bis-(halosulphonyl)- phenol of the general formula wherein Hal is a halogen atom, with an amine of the third general formula above.
GB4205468A 1968-09-04 1968-09-04 4-hydroxybenzenesulphonyl derivatives, the preparation thereof and compositions containing them Expired GB1223619A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB4205468A GB1223619A (en) 1968-09-04 1968-09-04 4-hydroxybenzenesulphonyl derivatives, the preparation thereof and compositions containing them

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB4205468A GB1223619A (en) 1968-09-04 1968-09-04 4-hydroxybenzenesulphonyl derivatives, the preparation thereof and compositions containing them

Publications (1)

Publication Number Publication Date
GB1223619A true GB1223619A (en) 1971-02-24

Family

ID=10422632

Family Applications (1)

Application Number Title Priority Date Filing Date
GB4205468A Expired GB1223619A (en) 1968-09-04 1968-09-04 4-hydroxybenzenesulphonyl derivatives, the preparation thereof and compositions containing them

Country Status (1)

Country Link
GB (1) GB1223619A (en)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3979203A (en) * 1972-01-19 1976-09-07 American Cyanamid Company Sulfonamido herbicidal compositions and plant control methods using the same
US4074059A (en) * 1972-01-19 1978-02-14 American Cyanamid Company Substituted-1-phenol-4-sulfonamides
FR2361064A1 (en) * 1976-08-13 1978-03-10 American Cyanamid Co Selective control of wild oats in cereals and sugar beet - with (2,6)-dihalophenol -(4)-sulphonamide herbicides
US5336681A (en) * 1988-06-13 1994-08-09 Ono Pharmaceutical Co., Ltd. Derivatives of p-substituted phenyl ester of pivalic acid
WO2007092558A2 (en) * 2006-02-08 2007-08-16 Wyeth Sulfonamide derivatives to treat infection with hepatitis c virus

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3979203A (en) * 1972-01-19 1976-09-07 American Cyanamid Company Sulfonamido herbicidal compositions and plant control methods using the same
US4074059A (en) * 1972-01-19 1978-02-14 American Cyanamid Company Substituted-1-phenol-4-sulfonamides
FR2361064A1 (en) * 1976-08-13 1978-03-10 American Cyanamid Co Selective control of wild oats in cereals and sugar beet - with (2,6)-dihalophenol -(4)-sulphonamide herbicides
US5336681A (en) * 1988-06-13 1994-08-09 Ono Pharmaceutical Co., Ltd. Derivatives of p-substituted phenyl ester of pivalic acid
US5403850A (en) * 1988-06-13 1995-04-04 Ono Pharmaceutical Co., Ltd. Derivatives of P-substituted phenyl ester of pivalic acid
WO2007092558A2 (en) * 2006-02-08 2007-08-16 Wyeth Sulfonamide derivatives to treat infection with hepatitis c virus
WO2007092558A3 (en) * 2006-02-08 2007-12-27 Wyeth Corp Sulfonamide derivatives to treat infection with hepatitis c virus

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