GB666578A - Process for the preparation of derivatives of 1, 2, 3 substituted pyrazolones and derivatives obtained by this process - Google Patents

Process for the preparation of derivatives of 1, 2, 3 substituted pyrazolones and derivatives obtained by this process

Info

Publication number
GB666578A
GB666578A GB699/49A GB69949A GB666578A GB 666578 A GB666578 A GB 666578A GB 699/49 A GB699/49 A GB 699/49A GB 69949 A GB69949 A GB 69949A GB 666578 A GB666578 A GB 666578A
Authority
GB
United Kingdom
Prior art keywords
pyrazolone
dimethyl
oxyethyl
phenyl
trichloro
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
GB699/49A
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 GB666578A publication Critical patent/GB666578A/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
    • C07D231/10—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
    • C07D231/54—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings condensed with carbocyclic rings or ring systems

Landscapes

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

Abstract

A process for the preparation of derivatives of 1,2,3-substituted pyrazolones from 1,2,3-trisubstituted - 4 - (b ,b ,b - trihalogen - a - R1111 - oxyethyl)-5-pyrazolones of the general formula <FORM:0666578/IV (b)/1> in which R, R1, and R11 denote alkyl or aryl radicles, R111 denotes chlorine or bromine, and R1111 denotes hydrogen or an acyl radical, is characterized by the fact that the 1,2,3-trisubstituted - 4 - (b ,b ,b - trihalogen - a - R1111-oxyethyl)-5-pyrazolone is heated to boiling point in the presence of an inorganic potassium or sodium base, so as to obtain an aldehyde having the formula <FORM:0666578/IV (b)/2> The 1,2,3-trisubstituted-4-(b ,b , b -trihalogen-a -R1111-oxyethyl)-5-pyrazolone may be prepared by reacting chloral or bromal hydrate and the corresponding 1,2,3-trisubstituted pyrazolone at 110 DEG -140 DEG C., the product being taken up in boiling water and recrystallized. Examples describe the preparation of 1-phenyl-2,3,-dimethyl-4-aldehyde-5-pyrazolone by reacting (1) 1-phenyl-2,3-dimethyl-4-(b ,b , b -trichloro-a -oxyethyl-5-pyrazolone; (2) 1-phenyl-2,3-dimethyl-4, (b ,b ,b - trichloro - a - acetoxyethyl) - 5 - pyrazolone and (3) 1-phenyl-2,3-dimethyl-4-(b ,b ,b - trichloro - a - oxyethyl) - 5 - pyrazolone with potassium carbonate solution; (4) 1-p-tolyl-2,3-dimethyl-4-aldehyde-5-pyrazolone by reacting 1-p-tolyl-2,3-dimethyl-4-(b ,b ,b -trichloro-a -oxyethyl) -5-pyrazolone with potassium carbonate; (5) the aldehyde of 1 : 3-diphenyl-2-methyl-5-pyrazolone by treating 1 : 3-diphenyl-2 - methyl - 4 - (b ,b ,b - trichloro - a - oxyethyl) - 5 - pyrazolone with sodium carbonate; (6) a mixture of 1-phenyl-2:3-dimethyl-4-aldehyde-5-pyrazolone and 4:41-bis-(1-phenyl-2:3-dimethyl-5-pyrazolone ethanoic acid by reacting 1-phenyl-2:3-dimethyl-4-(b ,b , b -trichloro-a -oxyethyl-5-pyrazolone with ethanolic alcoholic p potash. These two compounds are separated by chloroform extraction.
GB699/49A 1948-01-10 1949-01-10 Process for the preparation of derivatives of 1, 2, 3 substituted pyrazolones and derivatives obtained by this process Expired GB666578A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
BE666578X 1948-01-10

Publications (1)

Publication Number Publication Date
GB666578A true GB666578A (en) 1952-02-13

Family

ID=3877301

Family Applications (1)

Application Number Title Priority Date Filing Date
GB699/49A Expired GB666578A (en) 1948-01-10 1949-01-10 Process for the preparation of derivatives of 1, 2, 3 substituted pyrazolones and derivatives obtained by this process

Country Status (1)

Country Link
GB (1) GB666578A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1220858B (en) * 1958-12-09 1966-07-14 Bayer Ag Process for the preparation of N, N-dialkyl- or N-alkyl-N-aryl-substituted 4-aminomethylene pyrazolones- (5) and of 4-formyl-pyrazolones- (5) with unsubstituted 2-position
US4515944A (en) * 1981-08-20 1985-05-07 Kali-Chemie Pharma Gmbh 1,5-Diphenyl-2-haloalkylpyrazolin-3-one intermediates

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1220858B (en) * 1958-12-09 1966-07-14 Bayer Ag Process for the preparation of N, N-dialkyl- or N-alkyl-N-aryl-substituted 4-aminomethylene pyrazolones- (5) and of 4-formyl-pyrazolones- (5) with unsubstituted 2-position
US4515944A (en) * 1981-08-20 1985-05-07 Kali-Chemie Pharma Gmbh 1,5-Diphenyl-2-haloalkylpyrazolin-3-one intermediates

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