GB694204A - Improvements in or relating to the preparation of aldehydes of 1:2:3-trisubstituted pyrazolones - Google Patents

Improvements in or relating to the preparation of aldehydes of 1:2:3-trisubstituted pyrazolones

Info

Publication number
GB694204A
GB694204A GB30950/50A GB3095050A GB694204A GB 694204 A GB694204 A GB 694204A GB 30950/50 A GB30950/50 A GB 30950/50A GB 3095050 A GB3095050 A GB 3095050A GB 694204 A GB694204 A GB 694204A
Authority
GB
United Kingdom
Prior art keywords
hydrazide
phenyl
pyrazolone
aryl
carboxylic acid
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
GB30950/50A
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.)
LUXEMA
Original Assignee
LUXEMA
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 LUXEMA filed Critical LUXEMA
Publication of GB694204A publication Critical patent/GB694204A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/06—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D231/18—One oxygen or sulfur atom
    • C07D231/20—One oxygen atom attached in position 3 or 5
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D231/18—One oxygen or sulfur atom
    • C07D231/20—One oxygen atom attached in position 3 or 5
    • C07D231/22—One oxygen atom attached in position 3 or 5 with aryl radicals attached to ring nitrogen atoms

Abstract

In a process for the preparation of 1 : 2 : 3-trisubstituted pyrazolone aldehydes of the formula <FORM:0694204/IV (b)/1> in which R, R1 and R11 are alkyl or aryl radicals, a 1 : 2 : 3-trisubstituted pyrazolone carboxylic acid chloride is reacted with an aryl sulphone hydrazide (R111SO2.NH.NH2) or with hydrazine and subsequently with an aryl sulphonyl chloride to give the aryl sulphone hydrazide of the general formula <FORM:0694204/IV (b)/2> (R111 being an aryl radical) and that hydrazide is decomposed by heating in the presence of an alkali metal carbonate. As an organic solvent in the reaction of the aryl sulphonyl chloride there may be used a tertiary base, e.g. pyridine. The heating with alkali metal carbonate may be effected in a solvent e.g. an alcohol such as glycerol. In examples: 1-phenyl-2,3-dimethylpyrazolone-4-carboxylic acid benzene sulphone hydrazide is heated with sodium carbonate in glycerol solution to give 1-phenyl-2,3-dimethyl pyrazolone aldehyde. The 1-phenyl-2,3-dimethyl-pyrazolone-4-carboxylic acid benzene sulphone hydrazide is obtained by reacting 1-phenyl-2,3-dimethyl pyrazolone-4-carboxylic acid chloride with hydrazine hydroxide, and reacting the resultant hydrazide with benzene sulphonyl chloride. Alternatively it may be obtained by reacting the 1-phenyl-2,3-dimethyl pyrazolone-4-carboxylic acid chloride with benzene sulphone hydrazide. Alternative radicals at R, R1 and R11 may be methyl, ethyl, propyl, phenyl or naphthyl radicals.
GB30950/50A 1949-12-21 1950-12-19 Improvements in or relating to the preparation of aldehydes of 1:2:3-trisubstituted pyrazolones Expired GB694204A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
NL694204X 1949-12-21

Publications (1)

Publication Number Publication Date
GB694204A true GB694204A (en) 1953-07-15

Family

ID=19808820

Family Applications (1)

Application Number Title Priority Date Filing Date
GB30950/50A Expired GB694204A (en) 1949-12-21 1950-12-19 Improvements in or relating to the preparation of aldehydes of 1:2:3-trisubstituted pyrazolones

Country Status (1)

Country Link
GB (1) GB694204A (en)

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