GB931595A - Aminobenzyl sulfonylethanol compounds - Google Patents

Aminobenzyl sulfonylethanol compounds

Info

Publication number
GB931595A
GB931595A GB4227260A GB4227260A GB931595A GB 931595 A GB931595 A GB 931595A GB 4227260 A GB4227260 A GB 4227260A GB 4227260 A GB4227260 A GB 4227260A GB 931595 A GB931595 A GB 931595A
Authority
GB
United Kingdom
Prior art keywords
compounds
hydroxyethylsulphonylmethyl
compound
toluidine
methoxy
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
GB4227260A
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.)
GAF Chemicals Corp
Original Assignee
General Aniline and Film Corp
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 US858034A external-priority patent/US3118943A/en
Priority claimed from US858035A external-priority patent/US3019266A/en
Priority claimed from US858037A external-priority patent/US3019268A/en
Application filed by General Aniline and Film Corp filed Critical General Aniline and Film Corp
Publication of GB931595A publication Critical patent/GB931595A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C315/00—Preparation of sulfones; Preparation of sulfoxides
    • C07C315/04—Preparation of sulfones; Preparation of sulfoxides by reactions not involving the formation of sulfone or sulfoxide groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C317/00—Sulfones; Sulfoxides
    • C07C317/16—Sulfones; Sulfoxides having sulfone or sulfoxide groups and singly-bound oxygen atoms bound to the same carbon skeleton
    • C07C317/18—Sulfones; Sulfoxides having sulfone or sulfoxide groups and singly-bound oxygen atoms bound to the same carbon skeleton with sulfone or sulfoxide groups bound to acyclic carbon atoms of the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/10—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton
    • C07C323/11—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
    • C07C323/16—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton containing six-membered aromatic rings

Landscapes

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

Abstract

The invention comprises aminobenzene compounds containing at least one m-substituted -CH2SO2CH2CH2OH group, in particular such compounds of formula (I) wherein R1, R2, R3 and R4 may be H, halogen, lower alkyl or lower alkoxy ("lower" denotes 1 or 2 carbon atoms) and R2 may also be -CH2SO2CH2CH2OH. The compounds are synthesised <FORM:0931595/IV(a)/1> by (1) reacting a nitrobenzene compound with bischloromethyl ether, preferably using hydrated ZnCl2, (2) reacting the m-chloromethylnitrobenzene with mercaptoethanol in presence of an acid binding agent, (3) oxidizing the hydroxyethylmercaptomethyl compound to the corresponding hydroxyethylsulphonylmethyl compound with H2O2 and (4) reducing the nitro group to amino in the product. The examples describe the preparation of (a) 3:5-bis(2-hydroxyethylsulphonylmethyl)-4-toluidine (and its corresponding hydroxyethylsulphonylmethylnitrotoluene and hydroxyethylthiomethylnitrotoluene precursors) and of 3-(2-hydroxyethylsulphonylmethyl)-4-toluidine; (b) the intermediates 2 (and 4)-methoxy-5-nitrobenzylchloride and 2-methoxy-5-nitrobenzylthioethanol. Other suitable intermediates are listed in the Specification. Specifications 931,596 and U.S.A. 2,768,217 are referred to.
GB4227260A 1959-12-08 1960-12-08 Aminobenzyl sulfonylethanol compounds Expired GB931595A (en)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US85803659A 1959-12-08 1959-12-08
US858034A US3118943A (en) 1959-12-08 1959-12-08 Aminobenzylsulfonylethanol compounds
US858035A US3019266A (en) 1959-12-08 1959-12-08 Nitrobenzylsulfonylethanol compounds
US858037A US3019268A (en) 1959-12-08 1959-12-08 Nitrobenzylthioethanol compounds

Publications (1)

Publication Number Publication Date
GB931595A true GB931595A (en) 1963-07-17

Family

ID=27505928

Family Applications (1)

Application Number Title Priority Date Filing Date
GB4227260A Expired GB931595A (en) 1959-12-08 1960-12-08 Aminobenzyl sulfonylethanol compounds

Country Status (2)

Country Link
CH (1) CH401079A (en)
GB (1) GB931595A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4613704A (en) * 1983-12-01 1986-09-23 Hoechst Aktiengesellschaft Process for the preparation of 5-hydroxyethylsulfonyl-2-aminophenol (ethers)
EP0310944A2 (en) * 1987-10-03 1989-04-12 Hoechst Aktiengesellschaft Bisoxethylsulfonylmethyl anilines and process for their preparation

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4613704A (en) * 1983-12-01 1986-09-23 Hoechst Aktiengesellschaft Process for the preparation of 5-hydroxyethylsulfonyl-2-aminophenol (ethers)
EP0310944A2 (en) * 1987-10-03 1989-04-12 Hoechst Aktiengesellschaft Bisoxethylsulfonylmethyl anilines and process for their preparation
EP0310944A3 (en) * 1987-10-03 1990-01-10 Hoechst Aktiengesellschaft Bisoxethylsulfonylmethyl anilines and process for their preparation
US4960940A (en) * 1987-10-03 1990-10-02 Hoechst Aktiengesellschaft Bis(hydroxyethylsulfonylmethyl)anilines and a process for their preparation

Also Published As

Publication number Publication date
CH401079A (en) 1965-10-31

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