GB1174841A - A process for the preparation of Substituted Isothiazoles - Google Patents

A process for the preparation of Substituted Isothiazoles

Info

Publication number
GB1174841A
GB1174841A GB3406467A GB3406467A GB1174841A GB 1174841 A GB1174841 A GB 1174841A GB 3406467 A GB3406467 A GB 3406467A GB 3406467 A GB3406467 A GB 3406467A GB 1174841 A GB1174841 A GB 1174841A
Authority
GB
United Kingdom
Prior art keywords
alkyl
acid
give
product
substituted
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
GB3406467A
Inventor
Lee Cannon Cheney
Leonard Bruce Crast
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.)
Bristol Myers Co
Original Assignee
Bristol Myers 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 Bristol Myers Co filed Critical Bristol Myers Co
Publication of GB1174841A publication Critical patent/GB1174841A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D275/00—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings
    • C07D275/02—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings not condensed with other rings
    • C07D275/03—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings not condensed with other rings 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D499/00—Heterocyclic compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. penicillins, penems; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

1,174,841. Synthesizing 3,5-disubstituted isothiazole - 4 - carboxylic acids. BRISTOLMYERS CO. 25 July, 1967 [25 July, 1966], No. 34064/67. Compounds of formula wherein R, R<SP>2</SP> are each C 1-6 alkyl or Ar( = Ph, optionally mono-, di- or tri-substituted by F, Cl, Br, I, CF 3 , MeSO 2 , NO 2 , C 1-6 alkyl or/and C 1-6 alkoxy), are prepared by (a) halogenating RC(NH 2 ): CR<SP>1</SP>COR<SP>2</SP>(I) at 0-100‹ C. with PCl 5 , PCl 3 , SoCl 2 , SoBr 2 , PBr 3 or PBr 5 (R<SP>1</SP> being -CO 2 R<SP>3</SP>, -CN or -CONR<SP>4</SP>R<SP>5</SP>, where R<SP>3</SP> is C 1-6 alkyl or Ar and R<SP>4</SP>, R<SP>5</SP> are each H, C 1-6 alkyl or Ar; (b) reacting the product (presumably, e.g., RC(NH 2 ): CR<SP>1</SP>CCl: CH 2 , when R<SP>2</SP> is CH 3 and a chlorinating agent is used) at - 20‹ to 100‹ C. with H 2 S and/or MSH (M = alkali metal); (c) oxidizing the product (presumably, e.g. RC(NH 2 ): CR<SP>1</SP>C(: S)CH 3 ) at 0- 100‹ with O 2 , air, I 2 , Br 2 , Cl 2 , halogen + acid scavenger, H 2 O 2 , S, FeCl 3 , Na 2 S 2 O 8 , chloranil or 2,3-dichloro-5,6-dicyano-1,4-benzoquinone, to give a 3-R-4-R<SP>1</SP>-5-R<SP>2</SP>-isothiazole; and (d) hydrolysing the latter with acid or base at 0-100‹. The above compounds may be converted to the corresponding acid chlorides (with SOCl 2 ) and the latter reacted with 6-aminopenicillanic acid to give the corresponding 6- (4 - isothiazolylcarboxamido)penicillanic acids (isolated as the Na salts. Starting materials. Substituted alkenones (I, above) are prepared by hydrogenating 3-R-4-R<SP>1</SP>-5-R<SP>2</SP>-isoxazoles, which are themselves made by reacting (e.g. (a) α,2-dichloro-6-fluorobenzaldoxime (2 - chloro - 6 - fluorobenzaldoxime/ Cl 2 reaction product) or 2,6-dichlorobenzonitrile- N-oxide (2,6-dichlorobenzaldoxime) NaClO reaction product) with ethyl aceto- or propionoacetate; or (b) 3-(2,6-dichlorophenyl)-5-methylisoxazolecarboxylic acid chloride with NH 3 to give the corresponding amide which is converted to the corresponding nitrile with POCl 3 /Et 3 N.
GB3406467A 1966-07-25 1967-07-25 A process for the preparation of Substituted Isothiazoles Expired GB1174841A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US56740266A 1966-07-25 1966-07-25

Publications (1)

Publication Number Publication Date
GB1174841A true GB1174841A (en) 1969-12-17

Family

ID=24267007

Family Applications (1)

Application Number Title Priority Date Filing Date
GB3406467A Expired GB1174841A (en) 1966-07-25 1967-07-25 A process for the preparation of Substituted Isothiazoles

Country Status (5)

Country Link
BE (1) BE701763A (en)
CH (1) CH488720A (en)
DE (1) DE1670249B2 (en)
GB (1) GB1174841A (en)
NL (1) NL6710250A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4544752A (en) * 1980-09-22 1985-10-01 Eli Lilly And Company 3-Aryl-5-isothiazolecarboxylic acids and related compounds used to lower uric acid levels
JP2007537286A (en) * 2004-05-14 2007-12-20 アイアールエム・リミテッド・ライアビリティ・カンパニー Compounds and compositions as PPAR modulators

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4544752A (en) * 1980-09-22 1985-10-01 Eli Lilly And Company 3-Aryl-5-isothiazolecarboxylic acids and related compounds used to lower uric acid levels
JP2007537286A (en) * 2004-05-14 2007-12-20 アイアールエム・リミテッド・ライアビリティ・カンパニー Compounds and compositions as PPAR modulators

Also Published As

Publication number Publication date
BE701763A (en) 1968-01-24
NL6710250A (en) 1968-01-26
DE1670249B2 (en) 1974-07-18
DE1670249C3 (en) 1975-03-06
CH488720A (en) 1970-04-15
DE1670249A1 (en) 1972-03-02

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Legal Events

Date Code Title Description
PS Patent sealed
PLNP Patent lapsed through nonpayment of renewal fees