DE2002066A1 - Verfahren zur Herstellung von N-Trialkylsilyl-vinylsulfonamiden - Google Patents
Verfahren zur Herstellung von N-Trialkylsilyl-vinylsulfonamidenInfo
- Publication number
- DE2002066A1 DE2002066A1 DE19702002066 DE2002066A DE2002066A1 DE 2002066 A1 DE2002066 A1 DE 2002066A1 DE 19702002066 DE19702002066 DE 19702002066 DE 2002066 A DE2002066 A DE 2002066A DE 2002066 A1 DE2002066 A1 DE 2002066A1
- Authority
- DE
- Germany
- Prior art keywords
- alkyl
- trialkylsilyl
- dehydrohalogenation
- vinylsulfonamides
- substituted
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 14
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 238000006243 chemical reaction Methods 0.000 claims description 10
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 9
- -1 R 2 Ή Chemical group 0.000 claims description 8
- 238000006704 dehydrohalogenation reaction Methods 0.000 claims description 6
- 150000005840 aryl radicals Chemical class 0.000 claims description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 239000000010 aprotic solvent Substances 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 claims description 2
- 239000007795 chemical reaction product Substances 0.000 claims description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 claims 2
- APDDLLVYBXGBRF-UHFFFAOYSA-N [diethyl-(triethylsilylamino)silyl]ethane Chemical compound CC[Si](CC)(CC)N[Si](CC)(CC)CC APDDLLVYBXGBRF-UHFFFAOYSA-N 0.000 claims 1
- 150000001805 chlorine compounds Chemical class 0.000 claims 1
- 125000000547 substituted alkyl group Chemical group 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- JOXWSDNHLSQKCC-UHFFFAOYSA-N ethenesulfonamide Chemical class NS(=O)(=O)C=C JOXWSDNHLSQKCC-UHFFFAOYSA-N 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 229960003750 ethyl chloride Drugs 0.000 description 2
- XTHPWXDJESJLNJ-UHFFFAOYSA-N sulfurochloridic acid Chemical compound OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 2
- KNIUHBNRWZGIQQ-UHFFFAOYSA-N 7-diethoxyphosphinothioyloxy-4-methylchromen-2-one Chemical compound CC1=CC(=O)OC2=CC(OP(=S)(OCC)OCC)=CC=C21 KNIUHBNRWZGIQQ-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000005828 desilylation reaction Methods 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- IQLUAGKMPYRZCF-UHFFFAOYSA-N n-trimethylsilylpropan-1-amine Chemical compound CCCN[Si](C)(C)C IQLUAGKMPYRZCF-UHFFFAOYSA-N 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010517 secondary reaction Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000005420 sulfonamido group Chemical group S(=O)(=O)(N*)* 0.000 description 1
- 238000001149 thermolysis Methods 0.000 description 1
- 125000004665 trialkylsilyl group Chemical group 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/10—Compounds having one or more C—Si linkages containing nitrogen having a Si-N linkage
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19702002066 DE2002066A1 (de) | 1970-01-17 | 1970-01-17 | Verfahren zur Herstellung von N-Trialkylsilyl-vinylsulfonamiden |
| GB6200670A GB1334393A (en) | 1970-01-17 | 1970-12-31 | Process for the production of n-trialkylsilyl sulphonamides |
| NL7100330A NL7100330A (enExample) | 1970-01-17 | 1971-01-11 | |
| FR7101373A FR2075614A5 (enExample) | 1970-01-17 | 1971-01-15 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19702002066 DE2002066A1 (de) | 1970-01-17 | 1970-01-17 | Verfahren zur Herstellung von N-Trialkylsilyl-vinylsulfonamiden |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2002066A1 true DE2002066A1 (de) | 1971-07-22 |
Family
ID=5759891
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19702002066 Pending DE2002066A1 (de) | 1970-01-17 | 1970-01-17 | Verfahren zur Herstellung von N-Trialkylsilyl-vinylsulfonamiden |
Country Status (4)
| Country | Link |
|---|---|
| DE (1) | DE2002066A1 (enExample) |
| FR (1) | FR2075614A5 (enExample) |
| GB (1) | GB1334393A (enExample) |
| NL (1) | NL7100330A (enExample) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4910306A (en) * | 1987-11-09 | 1990-03-20 | The Dow Chemical Company | Preparation of substituted 1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonanilides |
| FR2637284A1 (fr) * | 1988-10-05 | 1990-04-06 | Elf Aquitaine | Methode de synthese de sulfonylimidures |
| US5003096A (en) * | 1989-05-30 | 1991-03-26 | The Dow Chemical Company | Preparation of substituted 1,2,4-triazolo[1,4-a]pyrimidine-2-sulfonanilides |
| US5256821A (en) * | 1988-10-05 | 1993-10-26 | Societe Nationale Elf Aquitaine | Method of synthesis of sulphonylimides |
-
1970
- 1970-01-17 DE DE19702002066 patent/DE2002066A1/de active Pending
- 1970-12-31 GB GB6200670A patent/GB1334393A/en not_active Expired
-
1971
- 1971-01-11 NL NL7100330A patent/NL7100330A/xx unknown
- 1971-01-15 FR FR7101373A patent/FR2075614A5/fr not_active Expired
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4910306A (en) * | 1987-11-09 | 1990-03-20 | The Dow Chemical Company | Preparation of substituted 1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonanilides |
| FR2637284A1 (fr) * | 1988-10-05 | 1990-04-06 | Elf Aquitaine | Methode de synthese de sulfonylimidures |
| EP0364340A1 (fr) * | 1988-10-05 | 1990-04-18 | Societe Nationale Elf Aquitaine | Méthode de synthèse de sulfonylimidures |
| WO1990003968A1 (fr) * | 1988-10-05 | 1990-04-19 | Societe Nationale Elf Aquitaine | Methode de synthese de sulfonylimidures |
| US5256821A (en) * | 1988-10-05 | 1993-10-26 | Societe Nationale Elf Aquitaine | Method of synthesis of sulphonylimides |
| US5003096A (en) * | 1989-05-30 | 1991-03-26 | The Dow Chemical Company | Preparation of substituted 1,2,4-triazolo[1,4-a]pyrimidine-2-sulfonanilides |
Also Published As
| Publication number | Publication date |
|---|---|
| NL7100330A (enExample) | 1971-07-20 |
| FR2075614A5 (enExample) | 1971-10-08 |
| GB1334393A (en) | 1973-10-17 |
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