GB940536A - New sulphur-containing naphthoquinones - Google Patents
New sulphur-containing naphthoquinonesInfo
- Publication number
- GB940536A GB940536A GB15398/62A GB1539862A GB940536A GB 940536 A GB940536 A GB 940536A GB 15398/62 A GB15398/62 A GB 15398/62A GB 1539862 A GB1539862 A GB 1539862A GB 940536 A GB940536 A GB 940536A
- Authority
- GB
- United Kingdom
- Prior art keywords
- naphthoquinone
- chloromethyl
- prepared
- alkyl
- compound
- 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
- 229930192627 Naphthoquinone Natural products 0.000 title abstract 3
- 150000002791 naphthoquinones Chemical class 0.000 title abstract 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 title 1
- 239000005864 Sulphur Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 abstract 11
- PYQUHGSCPCDFBQ-UHFFFAOYSA-N 2-(chloromethyl)-3-methylnaphthalene-1,4-dione Chemical compound C1=CC=C2C(=O)C(C)=C(CCl)C(=O)C2=C1 PYQUHGSCPCDFBQ-UHFFFAOYSA-N 0.000 abstract 5
- 125000000217 alkyl group Chemical group 0.000 abstract 5
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 abstract 4
- GYYQVIJEJDNZFI-UHFFFAOYSA-N 2,3-bis(chloromethyl)naphthalene-1,4-dione Chemical compound C1=CC=C2C(=O)C(CCl)=C(CCl)C(=O)C2=C1 GYYQVIJEJDNZFI-UHFFFAOYSA-N 0.000 abstract 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 3
- 125000003118 aryl group Chemical group 0.000 abstract 3
- 229910052700 potassium Inorganic materials 0.000 abstract 3
- 239000011591 potassium Substances 0.000 abstract 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 abstract 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 abstract 2
- 125000002947 alkylene group Chemical group 0.000 abstract 2
- 125000005843 halogen group Chemical group 0.000 abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- JCBJVAJGLKENNC-UHFFFAOYSA-M potassium ethyl xanthate Chemical compound [K+].CCOC([S-])=S JCBJVAJGLKENNC-UHFFFAOYSA-M 0.000 abstract 2
- DPIKZXAIPNGTLG-UHFFFAOYSA-N 2-chloro-3-(chloromethyl)naphthalene-1,4-dione Chemical compound C1=CC=C2C(=O)C(CCl)=C(Cl)C(=O)C2=C1 DPIKZXAIPNGTLG-UHFFFAOYSA-N 0.000 abstract 1
- QNTARNCGFNQQRP-UHFFFAOYSA-N 5-carbamothioylsulfanylpentyl carbamodithioate Chemical compound NC(=S)SCCCCCSC(N)=S QNTARNCGFNQQRP-UHFFFAOYSA-N 0.000 abstract 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 abstract 1
- -1 alkyl mercaptans Chemical class 0.000 abstract 1
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- 150000005840 aryl radicals Chemical group 0.000 abstract 1
- UENWRTRMUIOCKN-UHFFFAOYSA-N benzyl thiol Chemical compound SCC1=CC=CC=C1 UENWRTRMUIOCKN-UHFFFAOYSA-N 0.000 abstract 1
- 230000005494 condensation Effects 0.000 abstract 1
- 238000009833 condensation Methods 0.000 abstract 1
- MZGNSEAPZQGJRB-UHFFFAOYSA-N dimethyldithiocarbamic acid Chemical compound CN(C)C(S)=S MZGNSEAPZQGJRB-UHFFFAOYSA-N 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- AFCCDDWKHLHPDF-UHFFFAOYSA-M metam-sodium Chemical group [Na+].CNC([S-])=S AFCCDDWKHLHPDF-UHFFFAOYSA-M 0.000 abstract 1
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical group [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 abstract 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 abstract 1
- 229910052708 sodium Inorganic materials 0.000 abstract 1
- 239000011734 sodium Substances 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical group OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 abstract 1
- CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 abstract 1
- 125000003396 thiol group Chemical group [H]S* 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/20—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carbonic acid, or sulfur or nitrogen analogues thereof
- C07D295/21—Radicals derived from sulfur analogues of carbonic acid
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
- C07C319/14—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C329/00—Thiocarbonic acids; Halides, esters or anhydrides thereof
- C07C329/12—Dithiocarbonic acids; Derivatives thereof
- C07C329/14—Esters of dithiocarbonic acids
- C07C329/16—Esters of dithiocarbonic acids having sulfur atoms of dithiocarbonic groups bound to acyclic carbon atoms
-
- 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
- C07C335/30—Isothioureas
- C07C335/32—Isothioureas having sulfur atoms of isothiourea groups bound to acyclic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/16—Esters of thiophosphoric acids or thiophosphorous acids
- C07F9/165—Esters of thiophosphoric acids
- C07F9/1653—Esters of thiophosphoric acids with arylalkanols
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/16—Esters of thiophosphoric acids or thiophosphorous acids
- C07F9/165—Esters of thiophosphoric acids
- C07F9/177—Esters of thiophosphoric acids with cycloaliphatic alcohols
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/04—One of the condensed rings being a six-membered aromatic ring
- C07C2602/10—One of the condensed rings being a six-membered aromatic ring the other ring being six-membered, e.g. tetraline
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention relates to compounds of the formula <FORM:0940536/C2/1> in which X is an alkyl, aralkyl or aryl radical, which may be substituted by a group -N(Alkyl)2, COOH, COOAlkyl or C(O)N(Alkyl)2, or is a group -C(S)OAlkyl, -C(S)NH2, -C(S)NHAlkyl, -C(S)N(Alkyl)2, -C(S)N Alkylene (the nitrogen atom and the alkylene group forming a heterocyclic ring); -P(S)(O Alkyl)2, -C(NH)NH2, -C(S) Alkyl, -C(S)Aryl, -C(O)Alkyl or C(O)Aryl, R11 is a hydrogen atom or a methyl radical, R1 is a hydrogen or halogen atom or an alkyl, nitro or sulphonic acid group, R is a halogen atom, a methyl or ethyl group, an aryl group, or a group -C(R11)HSX, and n is 1-4. The compounds may be prepared by condensing an appropriately substituted naphthoquinone derivative carrying a 2-halogenmethyl or 2-a -halogen-ethyl group with an appropriate compound containing at least one mercapto group. The reaction may be effected at atmospheric temperature in a solvent, e.g. methanol or ethanol. In the examples, (1) the compound <FORM:0940536/C2/2> is prepared from 2-chloromethyl-3-methyl-1, 4-naphthoquinone and potassium ethyl xanthate; (2) the compound <FORM:0940536/C2/3> is prepared from 2, 3-bis-chloromethyl-1, 4-naphthoquinone and potassium ethyl xanthate; (3) the compound <FORM:0940536/C2/4> is prepared from 2-chloromethyl-3-methyl-1, 4-naphthoquinone and potassium O,O-diethylthionothiolphosphate; (4) the compound <FORM:0940536/C2/5> is prepared from 2-chloromethyl-3-methyl-1,4-naphthoquinone and potassium O,O-diethylthionothiolphosphate; (5) the compound <FORM:0940536/C2/6> is prepared from 2-chloromethyl-3-methyl-1,4- naphthoquinone and thiourea; (6) the compound <FORM:0940536/C2/7> is prepared from 2,3-bis-chloromethyl-1,4- naphthoquinone and thiourea; (7) the compound <FORM:0940536/C2/8> is prepared from 2-chloromethyl-3-methyl-1,4-naphthoquinone and potassium pentamethylene dithiocarbomate; (8) the compound <FORM:0940536/C2/9> is prepared from 2,3-bis-chloromethyl-1,4-naphthoquinone and sodium pentamethylene dithiocarbamate. Reference is made also to the condensation of the naphthoquinone derivatives with alkyl mercaptans, thiophenols, benzyl mercaptan, thioglycollic acid and sodium methyl- or dimethyl -dithiocarbamate. 2 - Chloromethyl - 3 -chloro-1,4- naphthoquinone is an additional specified starting material.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF33729A DE1154112B (en) | 1961-04-21 | 1961-04-21 | Process for the preparation of mercaptomethylnaphthoquinone derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB940536A true GB940536A (en) | 1963-10-30 |
Family
ID=7095220
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB15398/62A Expired GB940536A (en) | 1961-04-21 | 1962-04-19 | New sulphur-containing naphthoquinones |
Country Status (3)
| Country | Link |
|---|---|
| CH (1) | CH412867A (en) |
| DE (1) | DE1154112B (en) |
| GB (1) | GB940536A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3464986A (en) * | 1965-02-18 | 1969-09-02 | Ici Ltd | Thio-carbamyl-gamma-lactones |
| US3678167A (en) * | 1965-02-18 | 1972-07-18 | Ici Ltd | Fungicidal composition containing thio-carbamyl-v-lactones |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5371047A (en) * | 1976-12-07 | 1978-06-24 | Sankyo Co Ltd | Dithio carbamic acid derivs., process for their preparation, preventivesand remedies against mycoplasma infection cotng. the same as active constituents |
-
1961
- 1961-04-21 DE DEF33729A patent/DE1154112B/en active Pending
-
1962
- 1962-04-13 CH CH457762A patent/CH412867A/en unknown
- 1962-04-19 GB GB15398/62A patent/GB940536A/en not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3464986A (en) * | 1965-02-18 | 1969-09-02 | Ici Ltd | Thio-carbamyl-gamma-lactones |
| US3678167A (en) * | 1965-02-18 | 1972-07-18 | Ici Ltd | Fungicidal composition containing thio-carbamyl-v-lactones |
Also Published As
| Publication number | Publication date |
|---|---|
| CH412867A (en) | 1966-05-15 |
| DE1154112B (en) | 1963-09-12 |
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