DE2556039C2 - Verfahren zur Herstellung von N,N-Dialkylaminophenyl-chlorformiat-hydrochloriden - Google Patents
Verfahren zur Herstellung von N,N-Dialkylaminophenyl-chlorformiat-hydrochloridenInfo
- Publication number
- DE2556039C2 DE2556039C2 DE19752556039 DE2556039A DE2556039C2 DE 2556039 C2 DE2556039 C2 DE 2556039C2 DE 19752556039 DE19752556039 DE 19752556039 DE 2556039 A DE2556039 A DE 2556039A DE 2556039 C2 DE2556039 C2 DE 2556039C2
- Authority
- DE
- Germany
- Prior art keywords
- chloroformate
- hydrochlorides
- dialkylaminophenyl
- preparation
- hydrochloride
- 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 12
- IGWCIHCQFSETGG-UHFFFAOYSA-N carbonochloridic acid;hydron;chloride Chemical class Cl.OC(Cl)=O IGWCIHCQFSETGG-UHFFFAOYSA-N 0.000 title claims description 6
- 238000002360 preparation method Methods 0.000 title claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 title description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 12
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical compound NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 claims description 11
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 8
- 238000006243 chemical reaction Methods 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 4
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 27
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000000370 acceptor Substances 0.000 description 6
- -1 aromatic chloroformates Chemical class 0.000 description 6
- AOGYCOYQMAVAFD-UHFFFAOYSA-N chlorocarbonic acid Chemical class OC(Cl)=O AOGYCOYQMAVAFD-UHFFFAOYSA-N 0.000 description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 description 4
- 150000003840 hydrochlorides Chemical class 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- XAYFOYQUYGHVMH-UHFFFAOYSA-N (2-aminophenyl) carbamate Chemical class NC(=O)OC1=CC=CC=C1N XAYFOYQUYGHVMH-UHFFFAOYSA-N 0.000 description 2
- WHIVCTHFWLMAHI-UHFFFAOYSA-N (2-aminophenyl) carbonochloridate Chemical class C(OC1=C(C=CC=C1)N)(=O)Cl WHIVCTHFWLMAHI-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- 150000007529 inorganic bases Chemical class 0.000 description 2
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 150000003141 primary amines Chemical class 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 150000003512 tertiary amines Chemical class 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- MESJRHHDBDCQTH-UHFFFAOYSA-N 3-(dimethylamino)phenol Chemical compound CN(C)C1=CC=CC(O)=C1 MESJRHHDBDCQTH-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 125000005587 carbonate group Chemical group 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000007872 degassing Methods 0.000 description 1
- 239000002274 desiccant Substances 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- QXJIABOUHLYVHP-UHFFFAOYSA-N n-chloromethanamine Chemical compound CNCl QXJIABOUHLYVHP-UHFFFAOYSA-N 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000000590 parasiticidal effect Effects 0.000 description 1
- 239000004476 plant protection product Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7441452A FR2295012A1 (fr) | 1974-12-17 | 1974-12-17 | Chlorhydrates de chloroformiates d'amino phenols |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2556039A1 DE2556039A1 (de) | 1976-06-24 |
| DE2556039C2 true DE2556039C2 (de) | 1985-03-07 |
Family
ID=9146241
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19752556039 Expired DE2556039C2 (de) | 1974-12-17 | 1975-12-12 | Verfahren zur Herstellung von N,N-Dialkylaminophenyl-chlorformiat-hydrochloriden |
Country Status (9)
| Country | Link |
|---|---|
| BE (1) | BE836741A (enrdf_load_html_response) |
| DE (1) | DE2556039C2 (enrdf_load_html_response) |
| DK (1) | DK142809B (enrdf_load_html_response) |
| FR (1) | FR2295012A1 (enrdf_load_html_response) |
| GB (1) | GB1475259A (enrdf_load_html_response) |
| IE (1) | IE42287B1 (enrdf_load_html_response) |
| IT (1) | IT1051486B (enrdf_load_html_response) |
| LU (1) | LU74014A1 (enrdf_load_html_response) |
| NL (1) | NL7513504A (enrdf_load_html_response) |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE535835C (de) * | 1928-12-04 | 1931-10-27 | Hoffmann La Roche & Co Akt Ges | Verfahren zur Darstellung von mono- und disubstituierten Carbaminsaeureestern |
-
1974
- 1974-12-17 FR FR7441452A patent/FR2295012A1/fr active Granted
-
1975
- 1975-11-14 IE IE247875A patent/IE42287B1/en unknown
- 1975-11-19 NL NL7513504A patent/NL7513504A/xx not_active Application Discontinuation
- 1975-12-02 GB GB4945975A patent/GB1475259A/en not_active Expired
- 1975-12-11 IT IT7005675A patent/IT1051486B/it active
- 1975-12-12 DE DE19752556039 patent/DE2556039C2/de not_active Expired
- 1975-12-15 LU LU74014A patent/LU74014A1/xx unknown
- 1975-12-16 DK DK570375A patent/DK142809B/da not_active IP Right Cessation
- 1975-12-17 BE BE162830A patent/BE836741A/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| DK570375A (enrdf_load_html_response) | 1976-06-18 |
| LU74014A1 (enrdf_load_html_response) | 1977-07-01 |
| NL7513504A (nl) | 1976-06-21 |
| FR2295012A1 (fr) | 1976-07-16 |
| DK142809B (da) | 1981-02-02 |
| BE836741A (fr) | 1976-06-17 |
| IT1051486B (it) | 1981-04-21 |
| FR2295012B1 (enrdf_load_html_response) | 1979-02-23 |
| DE2556039A1 (de) | 1976-06-24 |
| IE42287L (en) | 1976-06-17 |
| IE42287B1 (en) | 1980-07-16 |
| DK142809C (enrdf_load_html_response) | 1981-08-24 |
| GB1475259A (en) | 1977-06-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |