GB1125629A - Process for preparing hydroxythiadiazoles and product thereby obtained - Google Patents
Process for preparing hydroxythiadiazoles and product thereby obtainedInfo
- Publication number
- GB1125629A GB1125629A GB46382/65A GB4638265A GB1125629A GB 1125629 A GB1125629 A GB 1125629A GB 46382/65 A GB46382/65 A GB 46382/65A GB 4638265 A GB4638265 A GB 4638265A GB 1125629 A GB1125629 A GB 1125629A
- Authority
- GB
- United Kingdom
- Prior art keywords
- reaction
- thionyl
- chloride
- halo
- trifluoromethyl
- 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
Links
- 238000004519 manufacturing process Methods 0.000 title 1
- SWFSRMBSDMJGOK-UHFFFAOYSA-N thiadiazol-4-ol Chemical class OC1=CSN=N1 SWFSRMBSDMJGOK-UHFFFAOYSA-N 0.000 title 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 abstract 4
- 150000004868 1,2,5-thiadiazoles Chemical class 0.000 abstract 3
- FIOJWGRGPONADF-UHFFFAOYSA-N (sulfinylamino)benzene Chemical compound O=S=NC1=CC=CC=C1 FIOJWGRGPONADF-UHFFFAOYSA-N 0.000 abstract 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 abstract 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 2
- 125000001475 halogen functional group Chemical group 0.000 abstract 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 abstract 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 2
- 239000012429 reaction media Substances 0.000 abstract 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 2
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 1
- FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 239000004480 active ingredient Substances 0.000 abstract 1
- 229910021529 ammonia Inorganic materials 0.000 abstract 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 239000000645 desinfectant Substances 0.000 abstract 1
- 238000001704 evaporation Methods 0.000 abstract 1
- 229930182817 methionine Natural products 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 1
- 239000011541 reaction mixture Substances 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 238000009738 saturating Methods 0.000 abstract 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 abstract 1
- 229920002554 vinyl polymer Polymers 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/01—Five-membered rings
- C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
- C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
- C07D285/10—1,2,5-Thiadiazoles; Hydrogenated 1,2,5-thiadiazoles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
Abstract
1,125,629. 1,2,5-Thiadiazole derivatives. ELI LILLY & CO. 2 Nov., 1965 [2 Nov., 1964], No. 46382/65. Heading C2C. [Also in Division A5] Substituted 1,2,5-thiadiazole derivatives of the general formula where R is a C 1-8 alkyl group, cycloalkyl having from 5 to 8 ring carbon atoms, #-C 1-4 -alkylmercaptoethyl, vinyl, phenyl optionally substituted by one or more methyl, halo, trifluoromethyl, nitro or methoxy group, or benzyl optionally substituted by one or more methyl, halo, trifluoromethyl, nitro or methoxy group, are prepared by reacting, in an inert reaction medium, a compound of the formula or an acid addition salt thereof, with thionyl chloride or thionyl aniline at a temperature sufficient to initiate reaction. The reaction with thionyl chloride is preferably carried out in the presence of chloroform, and the reaction medium employed for the reaction with thionyl aniline is preferably pyridine. The preferred temperature is between 60‹ and 120‹ C. The 1,2,5-thiadiazoles are employed as the active ingredients in disinfectant solutions. 3 - (Amino - 3 - carbamoylpropyl) - dimethylsulphonium chloride hydrochloride is prepared by reacting methionine with anhydrous hydrogen chloride in methanol, evaporating the reaction mixture to dryness, dissolving the residue in methanol and saturating with gaseous ammonia.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US40837764A | 1964-11-02 | 1964-11-02 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1125629A true GB1125629A (en) | 1968-08-28 |
Family
ID=23616047
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB46382/65A Expired GB1125629A (en) | 1964-11-02 | 1965-11-02 | Process for preparing hydroxythiadiazoles and product thereby obtained |
Country Status (6)
| Country | Link |
|---|---|
| BE (1) | BE671521A (en) |
| BR (1) | BR6574423D0 (en) |
| CH (1) | CH478831A (en) |
| DE (1) | DE1545776A1 (en) |
| FR (1) | FR1454655A (en) |
| GB (1) | GB1125629A (en) |
-
1965
- 1965-10-27 BE BE671521D patent/BE671521A/xx unknown
- 1965-10-28 FR FR36585A patent/FR1454655A/en not_active Expired
- 1965-10-29 BR BR174423/65A patent/BR6574423D0/en unknown
- 1965-10-29 CH CH1493665A patent/CH478831A/en not_active IP Right Cessation
- 1965-10-29 DE DE19651545776 patent/DE1545776A1/en active Pending
- 1965-11-02 GB GB46382/65A patent/GB1125629A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| BE671521A (en) | 1966-04-27 |
| BR6574423D0 (en) | 1973-08-14 |
| FR1454655A (en) | 1966-02-11 |
| CH478831A (en) | 1969-09-30 |
| DE1545776A1 (en) | 1969-07-31 |
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