CH505114A - Verfahren zur Herstellung von 2,4,5-Trichlorpyrimidin und 2,4,5,6-Tetrachlorpyrimidin - Google Patents
Verfahren zur Herstellung von 2,4,5-Trichlorpyrimidin und 2,4,5,6-TetrachlorpyrimidinInfo
- Publication number
- CH505114A CH505114A CH1478567A CH1478567A CH505114A CH 505114 A CH505114 A CH 505114A CH 1478567 A CH1478567 A CH 1478567A CH 1478567 A CH1478567 A CH 1478567A CH 505114 A CH505114 A CH 505114A
- Authority
- CH
- Switzerland
- Prior art keywords
- trichloropyrimidine
- tetrachloropyrimidine
- reaction
- preparation
- chlorine
- Prior art date
Links
- GIKMWFAAEIACRF-UHFFFAOYSA-N 2,4,5-trichloropyrimidine Chemical compound ClC1=NC=C(Cl)C(Cl)=N1 GIKMWFAAEIACRF-UHFFFAOYSA-N 0.000 title claims description 16
- 238000000034 method Methods 0.000 title claims description 14
- GVBHCMNXRKOJRH-UHFFFAOYSA-N 2,4,5,6-tetrachloropyrimidine Chemical compound ClC1=NC(Cl)=C(Cl)C(Cl)=N1 GVBHCMNXRKOJRH-UHFFFAOYSA-N 0.000 title claims description 12
- 238000002360 preparation method Methods 0.000 title claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 18
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 13
- 239000000460 chlorine Substances 0.000 claims description 13
- 229910052801 chlorine Inorganic materials 0.000 claims description 13
- 239000000203 mixture Substances 0.000 claims description 5
- AGSPXMVUFBBBMO-UHFFFAOYSA-N beta-aminopropionitrile Chemical class NCCC#N AGSPXMVUFBBBMO-UHFFFAOYSA-N 0.000 claims description 4
- 239000003701 inert diluent Substances 0.000 claims description 4
- 238000009281 ultraviolet germicidal irradiation Methods 0.000 claims description 3
- 230000001419 dependent effect Effects 0.000 claims 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 18
- 239000003085 diluting agent Substances 0.000 description 12
- 238000005660 chlorination reaction Methods 0.000 description 9
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 5
- 238000009835 boiling Methods 0.000 description 5
- UNIJBMUBHBAUET-UHFFFAOYSA-N 3-(methylamino)propanenitrile Chemical compound CNCCC#N UNIJBMUBHBAUET-UHFFFAOYSA-N 0.000 description 4
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 4
- PBKONEOXTCPAFI-UHFFFAOYSA-N 1,2,4-trichlorobenzene Chemical compound ClC1=CC=C(Cl)C(Cl)=C1 PBKONEOXTCPAFI-UHFFFAOYSA-N 0.000 description 3
- 150000005698 chloropyrimidines Chemical class 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 2
- 101150081514 Spef2 gene Proteins 0.000 description 2
- ISAKRJDGNUQOIC-UHFFFAOYSA-N Uracil Chemical compound O=C1C=CNC(=O)N1 ISAKRJDGNUQOIC-UHFFFAOYSA-N 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000004508 fractional distillation Methods 0.000 description 2
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 150000003230 pyrimidines Chemical class 0.000 description 2
- 230000005855 radiation Effects 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- PANVCEBTPSTUEL-UHFFFAOYSA-N 1,1,2,3,3-pentachloropropane Chemical compound ClC(Cl)C(Cl)C(Cl)Cl PANVCEBTPSTUEL-UHFFFAOYSA-N 0.000 description 1
- DMZRCHJVWAKCAX-UHFFFAOYSA-N 1,2,3,3,4,4,5,5-octachlorocyclopentene Chemical compound ClC1=C(Cl)C(Cl)(Cl)C(Cl)(Cl)C1(Cl)Cl DMZRCHJVWAKCAX-UHFFFAOYSA-N 0.000 description 1
- BETNPSBTDMBHCZ-UHFFFAOYSA-N 1-(chloromethyl)-2,4-dimethylbenzene Chemical compound CC1=CC=C(CCl)C(C)=C1 BETNPSBTDMBHCZ-UHFFFAOYSA-N 0.000 description 1
- UNCQVRBWJWWJBF-UHFFFAOYSA-N 2-chloropyrimidine Chemical compound ClC1=NC=CC=N1 UNCQVRBWJWWJBF-UHFFFAOYSA-N 0.000 description 1
- NHTURKUJYDHMIQ-UHFFFAOYSA-N 4,5-dichloropyrimidine Chemical compound ClC1=CN=CN=C1Cl NHTURKUJYDHMIQ-UHFFFAOYSA-N 0.000 description 1
- ZFTBZKVVGZNMJR-UHFFFAOYSA-N 5-chlorouracil Chemical compound ClC1=CNC(=O)NC1=O ZFTBZKVVGZNMJR-UHFFFAOYSA-N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- GGSUCNLOZRCGPQ-UHFFFAOYSA-N diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- VUNCWTMEJYMOOR-UHFFFAOYSA-N hexachlorocyclopentadiene Chemical compound ClC1=C(Cl)C(Cl)(Cl)C(Cl)=C1Cl VUNCWTMEJYMOOR-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000000985 reactive dye Substances 0.000 description 1
- 230000003330 sporicidal effect Effects 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- ZWZVWGITAAIFPS-UHFFFAOYSA-N thiophosgene Chemical compound ClC(Cl)=S ZWZVWGITAAIFPS-UHFFFAOYSA-N 0.000 description 1
- 229940035893 uracil Drugs 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/30—Halogen atoms or nitro radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Pyridine Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF0052633 | 1967-06-08 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH505114A true CH505114A (de) | 1971-03-31 |
Family
ID=7105602
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1478567A CH505114A (de) | 1967-06-08 | 1967-10-23 | Verfahren zur Herstellung von 2,4,5-Trichlorpyrimidin und 2,4,5,6-Tetrachlorpyrimidin |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US3506551A (en]) |
| AT (1) | AT276399B (en]) |
| BE (1) | BE706761A (en]) |
| CH (1) | CH505114A (en]) |
| DK (1) | DK117424B (en]) |
| ES (1) | ES346898A1 (en]) |
| GB (1) | GB1153096A (en]) |
| NL (1) | NL6715445A (en]) |
| NO (1) | NO120992B (en]) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2307863A1 (de) * | 1973-02-17 | 1974-08-22 | Bayer Ag | Verfahren zur herstellung von chlorpyrimidinen |
| US3997554A (en) * | 1975-03-05 | 1976-12-14 | The Dow Chemical Company | N,N-di(carbonyl chlorides) of N,N'-alkylene ureas |
| DE2725888A1 (de) * | 1977-06-08 | 1978-12-21 | Bayer Ag | Verfahren zur herstellung von 2,4,5-trichlorpyrimidin |
| US20060282051A1 (en) * | 2005-06-13 | 2006-12-14 | Susan Reichheld | Surgical towel having radiopaque element and methods for making same |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1164418B (de) * | 1960-11-26 | 1964-03-05 | Basf Ag | Verfahren zur Herstellung heterocyclischer Chlorverbindungen |
-
1967
- 1967-10-23 CH CH1478567A patent/CH505114A/de not_active IP Right Cessation
- 1967-10-26 GB GB48688/67A patent/GB1153096A/en not_active Expired
- 1967-10-27 AT AT972267A patent/AT276399B/de active
- 1967-10-31 US US679553A patent/US3506551A/en not_active Expired - Lifetime
- 1967-11-08 ES ES346898A patent/ES346898A1/es not_active Expired
- 1967-11-08 DK DK556767AA patent/DK117424B/da unknown
- 1967-11-14 NL NL6715445A patent/NL6715445A/xx unknown
- 1967-11-20 BE BE706761D patent/BE706761A/xx unknown
- 1967-11-22 NO NO170634A patent/NO120992B/no unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NL6715445A (en]) | 1968-12-09 |
| AT276399B (de) | 1969-11-25 |
| ES346898A1 (es) | 1969-01-16 |
| NO120992B (en]) | 1971-01-04 |
| DE1670877B2 (de) | 1975-08-07 |
| GB1153096A (en) | 1969-05-21 |
| DK117424B (da) | 1970-04-27 |
| DE1670877A1 (de) | 1971-02-18 |
| BE706761A (en]) | 1968-05-20 |
| US3506551A (en) | 1970-04-14 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |