GB584585A - Manufacture of derivatives of ªÐ-aminobenzenesulphonylguanidine - Google Patents

Manufacture of derivatives of ªÐ-aminobenzenesulphonylguanidine

Info

Publication number
GB584585A
GB584585A GB51945A GB51945A GB584585A GB 584585 A GB584585 A GB 584585A GB 51945 A GB51945 A GB 51945A GB 51945 A GB51945 A GB 51945A GB 584585 A GB584585 A GB 584585A
Authority
GB
United Kingdom
Prior art keywords
pyridine
guanidine
nitrobenzenesulphonylacetylguanidine
treated
aminobenzenesulphonylguanidine
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
GB51945A
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.)
BRITISH SCHERING RES LAB Ltd
PHILIP RUFUS CARTER
Original Assignee
BRITISH SCHERING RES LAB Ltd
PHILIP RUFUS CARTER
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 BRITISH SCHERING RES LAB Ltd, PHILIP RUFUS CARTER filed Critical BRITISH SCHERING RES LAB Ltd
Priority to GB51945A priority Critical patent/GB584585A/en
Publication of GB584585A publication Critical patent/GB584585A/en
Expired legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C311/00Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C311/50Compounds containing any of the groups, X being a hetero atom, Y being any atom
    • C07C311/52Y being a hetero atom
    • C07C311/64X and Y being nitrogen atoms, e.g. N-sulfonylguanidine

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Abstract

p-Acylamino-, p-nitro-, or p-amino-benzenesulphonylacylguanidines of the probable general formula <FORM:0584585/IV/1> wherein R represents -NH Acyl, -NO2 or -NH2 and R1 represents alkyl or aryl, are obtained by: (a) direct diacylation of p-aminobenzenesulphonylguanidine; (b) direct monoacylation of a p-acylaminobenzenesulphonyl-, p-aminobenzenesulphonylacyl-, p-nitrobenzenesulphonylacyl-, or p - nitrobenzenesulphonyl - guanidine; (c) the action of ammonia urea or ammonium carbonate on a p-acylaminobenzene-sulphonylacylmethylisothiourea; (d) condensing a p-acylaminobenzenesulphonylhalide-, or (e) a p-nitrobenzenesulphonylhalide-, with an acylguanidine or salt thereof; (f) reducing a p-nitrobenzenesulphonylacylguanidine to the corresponding p - amino compound. In examples: (1) p-aminobenzenesulphonylguanidine is boiled with acetic anhydride and pyridine to obtain p - acetylaminobenzenesulphonylacetyl - guanidine, which is similarly obtained by using as starting-materials either p-acetylaminobenzenesulphonyl-, or p - aminobenzenesulphonylacetyl-guanidine, pyridine being optional; (2) p-aminobenzenesulphonylguanidine is treated with propionic anhydride and pyridine, or p - propionylaminobenzenesulphonylguanidine with propionic anhydride to obtain the corresponding diacyl compound; (3) p-acetylaminobenzenesulphonylacetylmethylisothiourea is treated with ammonia to obtain p-acetylaminobenzenesulphonylacetylguanidine; (4) p-acetylaminobenzenesulphonyl chloride is heated with acetylguanidine and pyridine to obtain p-acetylaminobenzenesulphonylacetylguanidine; (5) p - acetylaminobenzenesulphonylguanidine is treated with propionic anhydride and pyridine to obtain p-acetylaminobenzenesulphonylpropionylguanidine; (6) p-nitrobenzenesulphonyl chloride and acetyl guanidine are together treated with pyridine to obtain p-nitrobenzenesulphonylacetylguanidine; (7) acetylguanidine acetate, in pyridine, is heated with p-nitrobenzenesulphonyl chloride to obtain p-nitrobenzenesulphonylacetylguanidine; (8) p-nitrobenzenesulphonylguanidine is heated under reflux with acetic anhydride and pyridine to obtain p-nitrobenzenesulphonylacetylguanidine; (9) p-nitrobenzenesulphonylacetylguanidine is hydrogenated at room temperature to obtain the corresponding p-amino compound; (10) p-nitrobenzenesulphonylguanidine and benzoicanhydride are heated to obtain crude p-nitrobenzenesulphonylbenzoylguanidine, which is hydrogenated as in (9) to obtain the corresponding p-amino compound. p - Acetylaminobenzenesulphonylacetylmethylisothiourea is obtained by heating p-acetylaminobenzenesulphonylmethylisothiourea with acetic anhydride in presence of anhydrous sodium acetate. p-Nitrobenzenesulphonylguanidine is obtained by condensing p-nitrobenzenesulphonyl chloride with guanidine nitrate in presence of sodium hydroxide.
GB51945A 1945-01-05 1945-01-05 Manufacture of derivatives of ªÐ-aminobenzenesulphonylguanidine Expired GB584585A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB51945A GB584585A (en) 1945-01-05 1945-01-05 Manufacture of derivatives of ªÐ-aminobenzenesulphonylguanidine

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB51945A GB584585A (en) 1945-01-05 1945-01-05 Manufacture of derivatives of ªÐ-aminobenzenesulphonylguanidine

Publications (1)

Publication Number Publication Date
GB584585A true GB584585A (en) 1947-01-17

Family

ID=9705791

Family Applications (1)

Application Number Title Priority Date Filing Date
GB51945A Expired GB584585A (en) 1945-01-05 1945-01-05 Manufacture of derivatives of ªÐ-aminobenzenesulphonylguanidine

Country Status (1)

Country Link
GB (1) GB584585A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3519415A (en) * 1968-06-17 1970-07-07 Monsanto Co Phytocidal n-(4-nitrophenylsulfonyl)-n'-(chlorosubstituted acetyl) ureas

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3519415A (en) * 1968-06-17 1970-07-07 Monsanto Co Phytocidal n-(4-nitrophenylsulfonyl)-n'-(chlorosubstituted acetyl) ureas

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