GB772159A - New fluorinated n,n-disubstituted thiourea compounds and process for their production - Google Patents
New fluorinated n,n-disubstituted thiourea compounds and process for their productionInfo
- Publication number
- GB772159A GB772159A GB10141/55A GB1014155A GB772159A GB 772159 A GB772159 A GB 772159A GB 10141/55 A GB10141/55 A GB 10141/55A GB 1014155 A GB1014155 A GB 1014155A GB 772159 A GB772159 A GB 772159A
- Authority
- GB
- United Kingdom
- Prior art keywords
- thiourea
- fluoro
- chlorophenyl
- isothiocyanate
- fluorinated
- 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/72—Nitrogen atoms
- C07D213/75—Amino or imino radicals, acylated by carboxylic or carbonic acids, or by sulfur or nitrogen analogues thereof, e.g. carbamates
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C335/00—Thioureas, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C335/04—Derivatives of thiourea
- C07C335/16—Derivatives of thiourea having nitrogen atoms of thiourea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/91—Dibenzofurans; Hydrogenated dibenzofurans
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention comprises fluorinated thioureas of the formula <FORM:0772159/IV(b)/1> (wherein R and R1 each represent a substituted or unsubstituted aryl or heterocyclic group and X is hydrogen, halogen, a substituted amino radical or the SO2NH2 group) and a process for their preparation by condensing an isothiocyanate X.R.N : C : S or F.R1.N : C : S with a primary amine F.R1.NH2 or X.R.NH2 respectively. Symmetrical thiourea derivatives of the above formula wherein X = F and R = R1 are also prepared by reacting carbon disulphide with a primary aromatic or heterocyclic amine which is fluorinated in the nucleus, in the presence of sulphur or an alkali metal hydroxide or alcoholate as catalyst. In examples: (1) p-fluoroaniline, carbon disulphide, sulphur and ethanol are refluxed together, the solvents removed and N : N1-bis-(4-fluorophenyl)-thiourea crystallized from ethanol; (2) p-fluoroaniline and p-chlorophenyl isothiocyanate are heated to 40-50 DEG C. to yield N-4-chlorophenyl-N1-41-fluorophenylthiourea; similarly are prepared the following N-4-fluorophenylthioureas: N1 - 41 - dimethylaminophenyl-, N1 - 41 - sulphamidophenyl-, N1 - 2 - pyridyl-, N1 - 41-phenoxyphenyl-, N1 - 21 - dibenzofuryl-, N1-21-methyl - 41 - rhodanophenyl-, and N1 - 21-chloro - 41 - rhodanophenyl-; also N - 2 - naphthyl - N1 - (51 - fluoro - 21 - methoxyphenyl)-thiourea (from b - naphthyl isothiocyanate and 5 - fluoro - 2 - methoxyaniline), N - 4 - tolyl - N1-(31 - fluoro - 61 - methoxyphenyl) thiourea and N - 4 - chlorophenyl - N1 - (41 - fluoro - 51 - tolyl) thiourea.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR772159X | 1954-04-28 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB772159A true GB772159A (en) | 1957-04-10 |
Family
ID=9193334
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB10141/55A Expired GB772159A (en) | 1954-04-28 | 1955-04-06 | New fluorinated n,n-disubstituted thiourea compounds and process for their production |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB772159A (en) |
-
1955
- 1955-04-06 GB GB10141/55A patent/GB772159A/en not_active Expired
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