DE2530278C3 - Carbamoylhalogenidverbindungen und Verfahren zu deren Herstellung - Google Patents
Carbamoylhalogenidverbindungen und Verfahren zu deren HerstellungInfo
- Publication number
- DE2530278C3 DE2530278C3 DE2530278A DE2530278A DE2530278C3 DE 2530278 C3 DE2530278 C3 DE 2530278C3 DE 2530278 A DE2530278 A DE 2530278A DE 2530278 A DE2530278 A DE 2530278A DE 2530278 C3 DE2530278 C3 DE 2530278C3
- Authority
- DE
- Germany
- Prior art keywords
- methyl
- preparation
- fluoride
- carbamoyl
- chloride
- 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
- 238000000034 method Methods 0.000 title claims description 29
- -1 Carbamoyl halide compounds Chemical class 0.000 title claims description 6
- 238000002360 preparation method Methods 0.000 title description 18
- 150000001875 compounds Chemical class 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims 3
- 125000004432 carbon atom Chemical group C* 0.000 claims 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 2
- 229910052801 chlorine Inorganic materials 0.000 claims 2
- 239000000460 chlorine Substances 0.000 claims 2
- 229910052731 fluorine Inorganic materials 0.000 claims 2
- 239000011737 fluorine Substances 0.000 claims 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
- 229910052794 bromium Inorganic materials 0.000 claims 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 21
- WRBUEDBPGZVHJQ-UHFFFAOYSA-N n-methylcarbamoyl fluoride Chemical compound CNC(F)=O WRBUEDBPGZVHJQ-UHFFFAOYSA-N 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 7
- 239000000047 product Substances 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 3
- VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 2
- UUNMUYGUJACXEF-UHFFFAOYSA-N butylsulfanyl thiohypochlorite Chemical compound CCCCSSCl UUNMUYGUJACXEF-UHFFFAOYSA-N 0.000 description 2
- PVXRCPDNJSFYBV-UHFFFAOYSA-N carbamoyl fluoride Chemical compound NC(F)=O PVXRCPDNJSFYBV-UHFFFAOYSA-N 0.000 description 2
- 229910000040 hydrogen fluoride Inorganic materials 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- 230000000749 insecticidal effect Effects 0.000 description 2
- KZXMYSAYNZSTGN-UHFFFAOYSA-N n-chloro-n-methylcarbamothioyl fluoride Chemical compound CN(Cl)C(F)=S KZXMYSAYNZSTGN-UHFFFAOYSA-N 0.000 description 2
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
- 150000007530 organic bases Chemical class 0.000 description 2
- FWMUJAIKEJWSSY-UHFFFAOYSA-N sulfur dichloride Chemical compound ClSCl FWMUJAIKEJWSSY-UHFFFAOYSA-N 0.000 description 2
- KSMPGMDHKGXOIN-UHFFFAOYSA-N (4-chlorophenyl)sulfanyl thiohypochlorite Chemical compound ClSSC1=CC=C(Cl)C=C1 KSMPGMDHKGXOIN-UHFFFAOYSA-N 0.000 description 1
- UTEYOINPNFCIPC-UHFFFAOYSA-N (4-tert-butylphenyl)sulfanyl thiohypochlorite Chemical compound CC(C)(C)C1=CC=C(SSCl)C=C1 UTEYOINPNFCIPC-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- GNXBFFHXJDZGEK-UHFFFAOYSA-N 4-tert-butylbenzenethiol Chemical compound CC(C)(C)C1=CC=C(S)C=C1 GNXBFFHXJDZGEK-UHFFFAOYSA-N 0.000 description 1
- QHPQWRBYOIRBIT-UHFFFAOYSA-N 4-tert-butylphenol Chemical compound CC(C)(C)C1=CC=C(O)C=C1 QHPQWRBYOIRBIT-UHFFFAOYSA-N 0.000 description 1
- QKRULLPHQQMEJH-UHFFFAOYSA-N N-[(2,4-dichlorophenyl)disulfanyl]-N-methylcarbamoyl fluoride Chemical compound FC(=O)N(C)SSC1=CC=C(Cl)C=C1Cl QKRULLPHQQMEJH-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- DQOFFVMVWHOTAJ-UHFFFAOYSA-N [carbonofluoridoyl(methyl)amino] thiohypochlorite Chemical compound ClSN(C)C(F)=O DQOFFVMVWHOTAJ-UHFFFAOYSA-N 0.000 description 1
- 239000000010 aprotic solvent Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- HAMGRBXTJNITHG-UHFFFAOYSA-N methyl isocyanate Chemical compound CN=C=O HAMGRBXTJNITHG-UHFFFAOYSA-N 0.000 description 1
- UTRHMUIOCZFTBW-UHFFFAOYSA-N methylsulfanyl thiohypochlorite Chemical compound CSSCl UTRHMUIOCZFTBW-UHFFFAOYSA-N 0.000 description 1
- LWFGVLVZEABWBZ-UHFFFAOYSA-N n-(butyldisulfanyl)-n-methylcarbamoyl fluoride Chemical compound CCCCSSN(C)C(F)=O LWFGVLVZEABWBZ-UHFFFAOYSA-N 0.000 description 1
- XJLUTTHMEGWGLP-UHFFFAOYSA-N n-[(4-tert-butylphenyl)disulfanyl]-n-methylcarbamoyl fluoride Chemical compound FC(=O)N(C)SSC1=CC=C(C(C)(C)C)C=C1 XJLUTTHMEGWGLP-UHFFFAOYSA-N 0.000 description 1
- VYDQQISAMFZBDX-UHFFFAOYSA-N n-chloro-n-methylcarbamothioyl chloride Chemical compound CN(Cl)C(Cl)=S VYDQQISAMFZBDX-UHFFFAOYSA-N 0.000 description 1
- FENADPBVPNVPCE-UHFFFAOYSA-N n-methyl-n-(2,4,4-trimethylpentan-2-yldisulfanyl)carbamoyl fluoride Chemical compound FC(=O)N(C)SSC(C)(C)CC(C)(C)C FENADPBVPNVPCE-UHFFFAOYSA-N 0.000 description 1
- KMKOWORUBLVRSA-UHFFFAOYSA-N n-methyl-n-(methyldisulfanyl)carbamoyl fluoride Chemical compound CSSN(C)C(F)=O KMKOWORUBLVRSA-UHFFFAOYSA-N 0.000 description 1
- FYGMOYDIOCUGGF-UHFFFAOYSA-N n-methyl-n-(octyldisulfanyl)carbamoyl fluoride Chemical compound CCCCCCCCSSN(C)C(F)=O FYGMOYDIOCUGGF-UHFFFAOYSA-N 0.000 description 1
- MNRSJQVDERRQQH-UHFFFAOYSA-N n-methyl-n-(phenyldisulfanyl)carbamoyl fluoride Chemical compound FC(=O)N(C)SSC1=CC=CC=C1 MNRSJQVDERRQQH-UHFFFAOYSA-N 0.000 description 1
- JFOANRPJGKDOQN-UHFFFAOYSA-N n-methyl-n-(propan-2-yldisulfanyl)carbamoyl fluoride Chemical compound CC(C)SSN(C)C(F)=O JFOANRPJGKDOQN-UHFFFAOYSA-N 0.000 description 1
- YWOZPEARHRJAKF-UHFFFAOYSA-N phenylsulfanyl thiohypochlorite Chemical compound ClSSC1=CC=CC=C1 YWOZPEARHRJAKF-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C333/00—Derivatives of thiocarbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C333/02—Monothiocarbamic acids; Derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C381/00—Compounds containing carbon and sulfur and having functional groups not covered by groups C07C301/00 - C07C337/00
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/486,631 US4093652A (en) | 1974-07-08 | 1974-07-08 | Process for the preparation of thiosulfenyl carbamoyl halides |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2530278A1 DE2530278A1 (de) | 1976-01-22 |
| DE2530278B2 DE2530278B2 (de) | 1978-01-05 |
| DE2530278C3 true DE2530278C3 (de) | 1978-09-14 |
Family
ID=23932634
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2530278A Expired DE2530278C3 (de) | 1974-07-08 | 1975-07-07 | Carbamoylhalogenidverbindungen und Verfahren zu deren Herstellung |
Country Status (15)
| Country | Link |
|---|---|
| US (2) | US4093652A (index.php) |
| JP (1) | JPS5132525A (index.php) |
| AU (1) | AU499177B2 (index.php) |
| BE (1) | BE831074A (index.php) |
| BR (1) | BR7504264A (index.php) |
| CA (1) | CA1060470A (index.php) |
| DE (1) | DE2530278C3 (index.php) |
| DK (1) | DK306875A (index.php) |
| ES (2) | ES439199A1 (index.php) |
| FR (1) | FR2299324A1 (index.php) |
| GB (1) | GB1477439A (index.php) |
| IL (1) | IL47663A0 (index.php) |
| IN (1) | IN141079B (index.php) |
| NL (1) | NL7508068A (index.php) |
| PL (1) | PL181890A1 (index.php) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US10857907B2 (en) * | 2018-04-05 | 2020-12-08 | Sears Manufacturing Co. | In-cushion seat swivel |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2671804A (en) * | 1948-12-28 | 1954-03-09 | Phillips Petroleum Co | Preparation and use of alkylene polyamine sulfenamides and thiosulefnamides |
| US3282950A (en) * | 1965-01-21 | 1966-11-01 | Olin Mathieson | Substituted 5-imino-1, 2, 4-thiadiazolidin-3-ones and process therefor |
| US3686320A (en) * | 1965-03-25 | 1972-08-22 | Fisons Pharmaceuticals Ltd | Bis-phenoxy compounds |
| US3879190A (en) * | 1972-05-24 | 1975-04-22 | Julius Jakob Fuchs | Herbicidal allophanimidates |
-
1974
- 1974-07-08 US US05/486,631 patent/US4093652A/en not_active Expired - Lifetime
-
1975
- 1975-06-10 AU AU81970/75A patent/AU499177B2/en not_active Expired
- 1975-06-13 CA CA229,248A patent/CA1060470A/en not_active Expired
- 1975-07-07 BR BR5458/75D patent/BR7504264A/pt unknown
- 1975-07-07 BE BE158044A patent/BE831074A/xx unknown
- 1975-07-07 ES ES439199A patent/ES439199A1/es not_active Expired
- 1975-07-07 GB GB2855375A patent/GB1477439A/en not_active Expired
- 1975-07-07 DK DK306875A patent/DK306875A/da unknown
- 1975-07-07 IN IN1317/CAL/75A patent/IN141079B/en unknown
- 1975-07-07 FR FR7521237A patent/FR2299324A1/fr active Granted
- 1975-07-07 JP JP50082851A patent/JPS5132525A/ja active Pending
- 1975-07-07 NL NL7508068A patent/NL7508068A/xx unknown
- 1975-07-07 DE DE2530278A patent/DE2530278C3/de not_active Expired
- 1975-07-07 PL PL18189075A patent/PL181890A1/xx unknown
- 1975-07-07 IL IL47663A patent/IL47663A0/xx unknown
- 1975-10-02 US US05/618,889 patent/US4091016A/en not_active Expired - Lifetime
-
1976
- 1976-04-29 ES ES447437A patent/ES447437A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5132525A (index.php) | 1976-03-19 |
| DK306875A (da) | 1976-01-09 |
| US4091016A (en) | 1978-05-23 |
| IN141079B (index.php) | 1977-01-15 |
| FR2299324A1 (fr) | 1976-08-27 |
| FR2299324B1 (index.php) | 1979-05-11 |
| AU499177B2 (en) | 1979-04-05 |
| GB1477439A (en) | 1977-06-22 |
| DE2530278A1 (de) | 1976-01-22 |
| BE831074A (fr) | 1976-01-07 |
| PL181890A1 (en) | 1978-01-16 |
| AU8197075A (en) | 1976-12-16 |
| ES447437A1 (es) | 1977-07-01 |
| US4093652A (en) | 1978-06-06 |
| NL7508068A (nl) | 1976-01-12 |
| IL47663A0 (en) | 1975-10-15 |
| BR7504264A (pt) | 1976-07-06 |
| CA1060470A (en) | 1979-08-14 |
| DE2530278B2 (de) | 1978-01-05 |
| ES439199A1 (es) | 1977-03-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| 8327 | Change in the person/name/address of the patent owner |
Owner name: UNION CARBIDE CORP., 06817 DANBURY, CONN., US |
|
| 8339 | Ceased/non-payment of the annual fee |