GB631269A - Improvements in or relating to pyrazole compounds - Google Patents

Improvements in or relating to pyrazole compounds

Info

Publication number
GB631269A
GB631269A GB11759/47A GB1175947A GB631269A GB 631269 A GB631269 A GB 631269A GB 11759/47 A GB11759/47 A GB 11759/47A GB 1175947 A GB1175947 A GB 1175947A GB 631269 A GB631269 A GB 631269A
Authority
GB
United Kingdom
Prior art keywords
pyrazolyl
methyl
acetal
benzaldehyde
chloroformylphenyl
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
GB11759/47A
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.)
EIDP Inc
Original Assignee
EI Du Pont de Nemours and Co
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 EI Du Pont de Nemours and Co filed Critical EI Du Pont de Nemours and Co
Publication of GB631269A publication Critical patent/GB631269A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • 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
    • C07D231/26—1-Phenyl-3-methyl-5- pyrazolones, unsubstituted or substituted on the phenyl ring

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

5 - Acyloxypyrazole amidoaldehydes and acetals of the formula <FORM:0631269/IV (b)/1> where Y is a carbonyl (-CO-) or sulphonyl (-SO2-) group (RY-being an acyl radical), R1 is a divalent organic radical linked by "hydrocarbon" carbon atoms, Z and Z1 are hydrogen, amidoaldehyde or amidoacetal groups at least one of Z and Z1 being amidoaldehyde or acetal, are prepared by treating a 5-acyloxypyrazole containing a carboxylic or sulphonic acid halide group in at least one of the 1- and 3-positions with an aminoaldehyde or an acetal thereof in which the acetal group is derived from an alkanol of 1-4 carbon atoms or a 1 : 2-or 1 : 3-dihydroxyalkane of 2-4 carbon atoms, in the presence of an acid binding agent. A preferred class of compound is <FORM:0631269/IV (b)/2> where R2 is hydrocarbon, B is as R1 but need not be the same. In all cases the acyl group RY- includes RCO- and RSO2-. Other preferred compounds are <FORM:0631269/IV (b)/3> where A1 is hydrocarbon attached to the N-atom through an aromatic nucleus, B1 is phenylene, and R3 is alkyl of 1-3 carbon atoms, alkoxy of 1 or 2 carbon atoms, phenyl, and methyl- or ethyl-phenyl. In all cases the hydrocarbon nuclei may be substituted by, e.g. methoxy, alkyl, aryl, halogen and nitro groups. The reaction is carried out at -10 DEG to +40 DEG C. (preferably -5 DEG to +5 DEG C.) in a solvent, e.g. dioxane, acetone, alcohol, or benzene, or mixtures of such solvents with water, in the presence of acid-binding agents, e.g. carbonates, sodium formate or acetate, or tertiary amines such as pyridine. Acetal groups may be hydrolysed to the free aldehyde with acid. Many starting materials are specified, both pyrazolyl acid chlorides, e.g. 1-(4-chloroformylmethoxyphenyl)-3-naphthyl-5-pyrazolyl chlorobenzoate, 1 - (21 - benzthiazolyl) - 3 - (p - chloroformylphenyl)-5-pyrazolyl benzoate, and 1-(21-methoxy - 51 - pyrazolyl methyl carbonate, and aminoaldehydes and acetals, e.g. 1-amino-2 : 2 - diethoxyethane and 2 - chloro - 4 -amino-benzaldehyde dimethyl acetal. In the examples, (1) m-[p-(5-ethylcarbonato-3-methyl-1-pyrazolyl) -benzamido]-benzaldehyde ethylene glycol acetal is prepared by reacting m-amino-benzaldehyde ethylene glycol acetal with 1-(41-chloroformylphenyl) - 3 - methyl - 5 - pyrazolyl ethyl carbonate in the presence of aqueous dioxan and potassium carbonate and the acetal group may then be hydrolysed; (2) m-[p-(5-benzoxy-3-methyl-1-pyrazolyl)-benzene-sulphonamido] - benzaldehyde ethylene glycol acetal is similarly prepared and hydrolysed; (3) m-[p-(5-benzoxy - 3 - methyl - 1 - pyrazolyl)-phenoxyacetamido]-benzaldehyde is obtained from m - aminobenzaldehyde - ethylene - glycol acetal and 1-(41-chloroformylmethoxyphenyl)-3-methyl-5-pyrazolyl benzoate; (4) 1-(41-carboxyphenyl)-3-methyl-5-pyrazolone is treated with acetic anhydride and sodium acetate to give 1-(41-carboxyphenyl)-3-methyl-5-pyrazolyl acetate, which is treated with thionyl chloride to give 1-(41-chloroformylphenyl)-3-methyl-5-pyrazolyl acetate, which is then reacted with m-aminobenzaldehyde dimethyl acetal; (5) m-[p-(5-benzoxy-3-methyl-1-pyrazolyl)-benzamido] benzaldehyde is obtained by reacting 1-(41-chloroformylphenyl)-3-methyl-5-pyrazolyl benzoate with m-aminobenzaldehyde ethylene-glycol acetal and hydrolysing the product; and (6) m - [p - (5 - ethylcarbonato - 1 - phenyl - 3 - pyrazolyl)-benzamido] benzaldehyde ethylene glycol acetal is obtained from m-aminobenzaldehyde ethylene glycol acetal and 1-phenyl-3-(41-chloroformylphenyl)-5-pyrazolyl ethyl carbonate, and the product may then be hydrolysed to give the free aldehyde. Specification 629,482 is referred to.ALSO:5-Acyloxypyrazole amidoaldehydes and acetals of the formula <FORM:0631269/IV (c)/1> (where Y is -CO- or -SO2-, RY- being acyl, R1 is a divalent radical or two such radicals joined by groups such as -O-, -S-, -CO-, &c., Z and Z1 are hydrogen, amidoaldehyde or amidoacetal groups, only one of which can be hydrogen) couple readily with diazo compounds.
GB11759/47A 1946-05-03 1947-05-01 Improvements in or relating to pyrazole compounds Expired GB631269A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US631269XA 1946-05-03 1946-05-03

Publications (1)

Publication Number Publication Date
GB631269A true GB631269A (en) 1949-10-31

Family

ID=22047098

Family Applications (1)

Application Number Title Priority Date Filing Date
GB11759/47A Expired GB631269A (en) 1946-05-03 1947-05-01 Improvements in or relating to pyrazole compounds

Country Status (1)

Country Link
GB (1) GB631269A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1993021160A1 (en) * 1992-04-13 1993-10-28 Dunlena Pty. Ltd. Arthropodicidal pyrazole sulfonates

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1993021160A1 (en) * 1992-04-13 1993-10-28 Dunlena Pty. Ltd. Arthropodicidal pyrazole sulfonates

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