GB1204406A - Process for the preparation of 2-alkoxy-5-n-(substituted or unsubstituted)-sulphamidobenzoic acids - Google Patents

Process for the preparation of 2-alkoxy-5-n-(substituted or unsubstituted)-sulphamidobenzoic acids

Info

Publication number
GB1204406A
GB1204406A GB04067/68A GB1406768A GB1204406A GB 1204406 A GB1204406 A GB 1204406A GB 04067/68 A GB04067/68 A GB 04067/68A GB 1406768 A GB1406768 A GB 1406768A GB 1204406 A GB1204406 A GB 1204406A
Authority
GB
United Kingdom
Prior art keywords
prepared
chlorosulphonyl
methoxy
nitrobenzene
nitro
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
GB04067/68A
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.)
Societe dEtudes Scientifiques et Industrielles de lIle de France SA
Original Assignee
Societe dEtudes Scientifiques et Industrielles de lIle de France SA
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
Priority claimed from FR100123A external-priority patent/FR1532332A/en
Priority claimed from FR101151A external-priority patent/FR1524388A/en
Priority claimed from FR101843A external-priority patent/FR1525352A/en
Application filed by Societe dEtudes Scientifiques et Industrielles de lIle de France SA filed Critical Societe dEtudes Scientifiques et Industrielles de lIle de France SA
Publication of GB1204406A publication Critical patent/GB1204406A/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
    • C07C309/01—Sulfonic acids
    • C07C309/28—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
    • C07C309/57—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing carboxyl groups bound to the carbon skeleton
    • C07C309/59—Nitrogen analogues of carboxyl groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof

Abstract

1,204,406. Sulphamide benzoic acid derivatives. SOC. D'ETUDES SCIENTIFIQUES ET INDUSTRIELLES DE L'ILE - DE - FRANCE. 22 March, 1968 [23 March, 1967; 31 March, 1967; 6 April, 1967], No. 14067/68. Heading C2C. The invention comprises compounds of the Formula I: in which A is an alkyl C 1 _ 5 or alkenyl radical C 1-5 and B is an amino or mono- or dialkylamino radical of low molecular weight C 1-5 in which the alkyl groups may be joined together by a -CH 2 - group or a N, O or S atom, to form a heterocycle having up to 5 carbon atoms, and the N atom may be linked to an alkyl group of low molecular weight C 1-5 , which may be prepared by treating a 2-alkoxy-5-chlorosulphonylnitrobenzene with ammonia or an amine, reducing the 2-alkoxy-5-N-(substituted or unsubstituted)-sulphamido-nitrobenzene formed, diazotizing the amino derivative formed and converting the diazo compound into a nitrile by the Sandmeyer method to obtain the nitrile I. This may subsequently be hydrolysed, if desired, to the acid. The preparations of 2- methoxy-5-sulphamido-benzonitrile, 2-ethoxy- 5 - dimethylsulphamido - benzonitrile and the corresponding benzoic acids are described. Heterocyclic ring systems defined by B include pyrrolidine, piperidine, imidazolidine, piperazine, morpholine or thiazolidine. p-Chlorosulphonyl-ethoxybenzene is prepared by treating ethoxybenzene with sulphuric chlorohydrin. 2 - Ethoxy - 5 - chlorosulphonyl-nitrobenzene is prepared by nitrating p-chlorosulphonyl-ethoxybenzene. 2 - Methoxy - 5 - chlorosulphonyl - nitrobenzene is prepared by treating the sodium or ammonium salt of 3-nitro-4-methoxy-benzene sulphonic acid with phosphorus pentachloride. Ammonium 3 - nitro - 4 - methoxybenzene sulphonite is prepared by reacting ammonia with 2 - methoxy - 5 - chlorosulphonyl - nitrobenzene which is prepared by reacting sulphuric chlorohydrin with 2-nitro anisole which is prepared by reacting o-nitrophenol with dimethyl sulphate. Sodium 3 - nitro - 4 - methoxybenzene sulphonate is prepared by reacting phenol with sulphuric acid and sodium nitrate.
GB04067/68A 1967-03-23 1968-03-22 Process for the preparation of 2-alkoxy-5-n-(substituted or unsubstituted)-sulphamidobenzoic acids Expired GB1204406A (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
FR100123A FR1532332A (en) 1967-03-23 1967-03-23 New process for preparing 2-alkoxy-5-sulfamido-benzoic acids
FR101151A FR1524388A (en) 1967-03-31 1967-03-31 New process for preparing 2-alkoxy-5-sulfamido-benzoic acids
FR101843A FR1525352A (en) 1967-04-06 1967-04-06 Process for preparing 2-alkoxy-5-sulfamido-benzoic acids

Publications (1)

Publication Number Publication Date
GB1204406A true GB1204406A (en) 1970-09-09

Family

ID=27243897

Family Applications (1)

Application Number Title Priority Date Filing Date
GB04067/68A Expired GB1204406A (en) 1967-03-23 1968-03-22 Process for the preparation of 2-alkoxy-5-n-(substituted or unsubstituted)-sulphamidobenzoic acids

Country Status (10)

Country Link
BE (1) BE711978A (en)
CH (1) CH486431A (en)
ES (1) ES350986A1 (en)
GB (1) GB1204406A (en)
IE (1) IE31981B1 (en)
IL (1) IL29627A (en)
IT (1) IT1052281B (en)
MC (1) MC705A1 (en)
OA (1) OA02767A (en)
YU (3) YU32182B (en)

Also Published As

Publication number Publication date
YU277079A (en) 1982-10-31
YU36698B (en) 1984-08-31
ES350986A1 (en) 1969-12-01
IE31981B1 (en) 1973-03-07
CH486431A (en) 1970-02-28
OA02767A (en) 1970-12-15
IL29627A (en) 1972-03-28
YU32182B (en) 1974-06-30
YU117573A (en) 1982-06-18
IE31981L (en) 1968-09-23
YU64668A (en) 1973-12-31
MC705A1 (en) 1968-12-17
IT1052281B (en) 1981-06-20
BE711978A (en) 1968-09-11

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Legal Events

Date Code Title Description
PS Patent sealed
PCNP Patent ceased through non-payment of renewal fee