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GB988956A - Cyano-substituted thiazole compounds - Google Patents

Cyano-substituted thiazole compounds

Info

Publication number
GB988956A
GB988956A GB2724462A GB2724462A GB988956A GB 988956 A GB988956 A GB 988956A GB 2724462 A GB2724462 A GB 2724462A GB 2724462 A GB2724462 A GB 2724462A GB 988956 A GB988956 A GB 988956A
Authority
GB
United Kingdom
Prior art keywords
thiazole
thiadiazole
methyl
cyano
cyanothiazole
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
GB2724462A
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.)
Merck and Co Inc
Original Assignee
Merck and Co Inc
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 Merck and Co Inc filed Critical Merck and Co Inc
Publication of GB988956A publication Critical patent/GB988956A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole 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
    • C07D277/56—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Thiazole And Isothizaole Compounds (AREA)
  • Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)

Abstract

Cyano-substituted thiazoles, isothiazoles, or thidiazoles are prepared by contacting a vapour mixture comprising ammonia, oxygen, and a C1-5 alkyl substituted thiazole, isothiazole or thiadiazole with a heated oxide of a metal with atomic weight between 50 and 100 from the Periodic Group Ib-VIIb and VIII. Compounds of formulae <FORM:0988956/C2/1> are specified where R is a C1-3 alkyl, particularly 2 methyl thiazole, 2-ethyl thiazoles, and 4- and 5-methyl thiazole, 4-methyl (1,2,3-thiadiazole), 5 - propyl (1,2,3 - thiadiazole), 3 - methyl (1,2,5 - thiadiazole) 3 - propyl and 5 - methyl isothiazoles. Oxides of vanadium, chromium, iron, cobalt, copper, zirconium, niobium and molybdenum are mentioned and alkali metal salts and alkaline earth metal oxides may be included. Examples describe the preparation of 4-cyanothiazole, 2-cyano thiazole, 4-cyanoisothiazole, and 5-cyano-1,2,3 thiadiazole. 4-cyanothiazole may be reacted with aniline to yield N-phenyl (thiazole-4-amidine) hydrochloride, which is reacted with hypochlorite to form N - chloro - N1 - phenyl (thiazole - 4-amidine), which is hydrolysed to 2-(41-thiazolyl)-benzimidazole.
GB2724462A 1961-07-24 1962-07-16 Cyano-substituted thiazole compounds Expired GB988956A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US12595661A 1961-07-24 1961-07-24
US17799762A 1962-03-07 1962-03-07

Publications (1)

Publication Number Publication Date
GB988956A true GB988956A (en) 1965-04-14

Family

ID=26824132

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2724462A Expired GB988956A (en) 1961-07-24 1962-07-16 Cyano-substituted thiazole compounds

Country Status (5)

Country Link
BR (1) BR6241052D0 (en)
DE (1) DE1198369B (en)
DK (1) DK118082B (en)
GB (1) GB988956A (en)
SE (1) SE309596B (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4055514A (en) * 1976-03-15 1977-10-25 Merck & Co., Inc. Catalyst for preparation of 4-cyanothiazole
US4055511A (en) * 1976-03-15 1977-10-25 Merck & Co., Inc. Catalyst for preparation of 4-cyanothiazole

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NZ197767A (en) * 1980-08-04 1983-04-12 Merck & Co Inc Ammoxidation catalyst containing manganese chromium and molybdenum oxides

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2499055A (en) * 1946-04-02 1950-02-28 Allied Chem & Dye Corp Production of nitriles
GB807485A (en) * 1956-11-10 1959-01-14 Distillers Co Yeast Ltd The production of aromatic nitriles and imides

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4055514A (en) * 1976-03-15 1977-10-25 Merck & Co., Inc. Catalyst for preparation of 4-cyanothiazole
US4055511A (en) * 1976-03-15 1977-10-25 Merck & Co., Inc. Catalyst for preparation of 4-cyanothiazole

Also Published As

Publication number Publication date
BR6241052D0 (en) 1973-05-10
DE1198369B (en) 1965-08-12
SE309596B (en) 1969-03-31
DK118082B (en) 1970-07-06

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