IL30984A - Thiadiazolinonyl-carbamyl-chlorides and process for their preparation - Google Patents

Thiadiazolinonyl-carbamyl-chlorides and process for their preparation

Info

Publication number: IL30984A
Authority: IL; Israel
Prior art keywords: formula; thiosemicarbazide; phosgene; reaction; substituted
Prior art date: 1967-12-06

Application number

IL30984A

Other languages

English (en)

Other versions

IL30984A0 (en

Original Assignee

Bayer Ag

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.)

1967-12-06

Filing date

1968-10-31

Publication date

1972-02-29

1967-12-06 Priority claimed from DE19671670956 external-priority patent/DE1670956A1/de

1968-10-31 Application filed by Bayer Ag filed Critical Bayer Ag

1969-01-29 Publication of IL30984A0 publication Critical patent/IL30984A0/xx

1972-02-29 Publication of IL30984A publication Critical patent/IL30984A/en

Links

238000000034 method Methods 0.000 title claims description 15
230000008569 process Effects 0.000 title claims description 13
238000002360 preparation method Methods 0.000 title description 2
238000006243 chemical reaction Methods 0.000 claims description 23
YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 22
-1 alkenyl radical Chemical class 0.000 claims description 13
150000001875 compounds Chemical class 0.000 claims description 12
125000003545 alkoxy group Chemical group 0.000 claims description 8
125000000217 alkyl group Chemical group 0.000 claims description 8
BRWIZMBXBAOCCF-UHFFFAOYSA-N hydrazinecarbothioamide Chemical compound NNC(N)=S BRWIZMBXBAOCCF-UHFFFAOYSA-N 0.000 claims description 8
125000004432 carbon atom Chemical group C* 0.000 claims description 7
CKDWPUIZGOQOOM-UHFFFAOYSA-N Carbamyl chloride Chemical class NC(Cl)=O CKDWPUIZGOQOOM-UHFFFAOYSA-N 0.000 claims description 6
239000002904 solvent Substances 0.000 claims description 6
239000003960 organic solvent Substances 0.000 claims description 5
125000000753 cycloalkyl group Chemical group 0.000 claims description 4
229910052736 halogen Inorganic materials 0.000 claims description 4
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
125000001188 haloalkyl group Chemical group 0.000 claims description 3
150000002367 halogens Chemical group 0.000 claims description 3
239000000543 intermediate Substances 0.000 claims description 3
238000004519 manufacturing process Methods 0.000 claims description 3
125000002877 alkyl aryl group Chemical group 0.000 claims description 2
125000003118 aryl group Chemical group 0.000 claims description 2
150000005840 aryl radicals Chemical class 0.000 claims description 2
125000000392 cycloalkenyl group Chemical group 0.000 claims description 2
239000002917 insecticide Substances 0.000 claims description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
229910052799 carbon Inorganic materials 0.000 claims 1
150000008280 chlorinated hydrocarbons Chemical class 0.000 claims 1
125000005843 halogen group Chemical group 0.000 claims 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 6
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
238000010438 heat treatment Methods 0.000 description 4
239000000725 suspension Substances 0.000 description 4
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
125000003277 amino group Chemical group 0.000 description 3
239000007795 chemical reaction product Substances 0.000 description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
239000002244 precipitate Substances 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
238000009835 boiling Methods 0.000 description 2
238000001816 cooling Methods 0.000 description 2
239000003085 diluting agent Substances 0.000 description 2
150000002391 heterocyclic compounds Chemical class 0.000 description 2
239000000203 mixture Substances 0.000 description 2
LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
239000000047 product Substances 0.000 description 2
238000001953 recrystallisation Methods 0.000 description 2
229910000033 sodium borohydride Inorganic materials 0.000 description 2
239000012279 sodium borohydride Substances 0.000 description 2
230000002269 spontaneous effect Effects 0.000 description 2
239000011593 sulfur Substances 0.000 description 2
229910052717 sulfur Inorganic materials 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
230000008719 thickening Effects 0.000 description 2
150000003583 thiosemicarbazides Chemical class 0.000 description 2
LZDKZFUFMNSQCJ-UHFFFAOYSA-N 1,2-diethoxyethane Chemical compound CCOCCOCC LZDKZFUFMNSQCJ-UHFFFAOYSA-N 0.000 description 1
KPZGRMZPZLOPBS-UHFFFAOYSA-N 1,3-dichloro-2,2-bis(chloromethyl)propane Chemical compound ClCC(CCl)(CCl)CCl KPZGRMZPZLOPBS-UHFFFAOYSA-N 0.000 description 1
WVSUVWIWVARAIS-UHFFFAOYSA-N 1-methyl-3-(propan-2-ylideneamino)thiourea Chemical compound CNC(=S)NN=C(C)C WVSUVWIWVARAIS-UHFFFAOYSA-N 0.000 description 1
PTVZQOAHCSKAAS-UHFFFAOYSA-N 4-methyl-3-thiosemicarbazide Chemical compound CNC(=S)NN PTVZQOAHCSKAAS-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 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 description 1
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
150000001540 azides Chemical class 0.000 description 1
XEVRDFDBXJMZFG-UHFFFAOYSA-N carbonyl dihydrazine Chemical compound NNC(=O)NN XEVRDFDBXJMZFG-UHFFFAOYSA-N 0.000 description 1
230000008859 change Effects 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
239000013078 crystal Substances 0.000 description 1
230000006837 decompression Effects 0.000 description 1
229940042396 direct acting antivirals thiosemicarbazones Drugs 0.000 description 1
238000004821 distillation Methods 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
125000003106 haloaryl group Chemical group 0.000 description 1
125000000623 heterocyclic group Chemical group 0.000 description 1
229910000041 hydrogen chloride Inorganic materials 0.000 description 1
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
239000013067 intermediate product Substances 0.000 description 1
238000011835 investigation Methods 0.000 description 1
150000002540 isothiocyanates Chemical class 0.000 description 1
239000003350 kerosene Substances 0.000 description 1
239000007788 liquid Substances 0.000 description 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
239000011814 protection agent Substances 0.000 description 1
239000012264 purified product Substances 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
230000009257 reactivity Effects 0.000 description 1
230000009467 reduction Effects 0.000 description 1
238000010992 reflux Methods 0.000 description 1
238000010517 secondary reaction Methods 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000007858 starting material Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
150000003584 thiosemicarbazones Chemical class 0.000 description 1
230000001052 transient effect Effects 0.000 description 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
- C07D285/12—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

IL30984A 1967-12-06 1968-10-31 Thiadiazolinonyl-carbamyl-chlorides and process for their preparation IL30984A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19671670956 DE1670956A1 (de)	1967-12-06	1967-12-06	Carbamidsaeurechloride von Thiadiazolinonen sowie Verfahren zu ihrer Herstellung

Publications (2)

Publication Number	Publication Date
IL30984A0 IL30984A0 (en)	1969-01-29
IL30984A true IL30984A (en)	1972-02-29

Family

ID=5686353

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL30984A IL30984A (en)	1967-12-06	1968-10-31	Thiadiazolinonyl-carbamyl-chlorides and process for their preparation

Country Status (6)

Country	Link
BE (1)	BE725051A (de)
CH (1)	CH509338A (de)
ES (1)	ES361137A1 (de)
FR (1)	FR1594943A (de)
GB (1)	GB1184318A (de)
IL (1)	IL30984A (de)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4911745A (en) *	1987-07-24	1990-03-27	Ici Americas Inc.	Novel 2-(substituted imino)-1,3,4-dihydrothladiazoles

1968
- 1968-10-30 CH CH1621768A patent/CH509338A/de not_active IP Right Cessation
- 1968-10-31 IL IL30984A patent/IL30984A/en unknown
- 1968-11-12 GB GB53591/68A patent/GB1184318A/en not_active Expired
- 1968-12-06 BE BE725051D patent/BE725051A/xx unknown
- 1968-12-06 ES ES361137A patent/ES361137A1/es not_active Expired
- 1968-12-06 FR FR1594943D patent/FR1594943A/fr not_active Expired

Also Published As

Publication number	Publication date
GB1184318A (en)	1970-03-11
IL30984A0 (en)	1969-01-29
ES361137A1 (es)	1970-12-16
FR1594943A (de)	1970-06-08
CH509338A (de)	1971-06-30
BE725051A (de)	1969-06-06

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