PL83653B1 - - Google Patents
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- Publication number
- PL83653B1 PL83653B1 PL1972154895A PL15489572A PL83653B1 PL 83653 B1 PL83653 B1 PL 83653B1 PL 1972154895 A PL1972154895 A PL 1972154895A PL 15489572 A PL15489572 A PL 15489572A PL 83653 B1 PL83653 B1 PL 83653B1
- Authority
- PL
- Poland
- Prior art keywords
- formula
- pattern
- model
- acid
- esters
- Prior art date
Links
- -1 N-substituted N-chloromethylcarbamic acids Chemical class 0.000 claims description 40
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 18
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 13
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 9
- 150000002148 esters Chemical class 0.000 claims description 9
- 229930040373 Paraformaldehyde Natural products 0.000 claims description 8
- 229920002866 paraformaldehyde Polymers 0.000 claims description 8
- 150000007970 thio esters Chemical class 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 7
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000000304 alkynyl group Chemical group 0.000 claims description 3
- 125000000262 haloalkenyl group Chemical group 0.000 claims description 3
- 125000001188 haloalkyl group Chemical group 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 125000003107 substituted aryl group Chemical group 0.000 claims description 3
- OVSKIKFHRZPJSS-UHFFFAOYSA-N 2,4-D Chemical compound OC(=O)COC1=CC=C(Cl)C=C1Cl OVSKIKFHRZPJSS-UHFFFAOYSA-N 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 125000000232 haloalkynyl group Chemical group 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 229910052717 sulfur Chemical group 0.000 claims description 2
- 239000011593 sulfur Chemical group 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 20
- 239000002253 acid Substances 0.000 description 13
- 238000006243 chemical reaction Methods 0.000 description 11
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 238000009835 boiling Methods 0.000 description 7
- 238000004821 distillation Methods 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- 239000007858 starting material Substances 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- 239000003085 diluting agent Substances 0.000 description 4
- 125000005843 halogen group Chemical group 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 3
- 229940112021 centrally acting muscle relaxants carbamic acid ester Drugs 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 125000000753 cycloalkyl group Chemical group 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 239000011737 fluorine Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 150000005840 aryl radicals Chemical class 0.000 description 2
- 125000004104 aryloxy group Chemical group 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 150000001805 chlorine compounds Chemical class 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 238000003776 cleavage reaction Methods 0.000 description 2
- 125000004494 ethyl ester group Chemical group 0.000 description 2
- GZXSDYYWLZERLF-UHFFFAOYSA-N ethyl n-ethylcarbamate Chemical compound CCNC(=O)OCC GZXSDYYWLZERLF-UHFFFAOYSA-N 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 150000004702 methyl esters Chemical class 0.000 description 2
- NYXHSRNBKJIQQG-UHFFFAOYSA-N methyl n-methylcarbamate Chemical compound CNC(=O)OC NYXHSRNBKJIQQG-UHFFFAOYSA-N 0.000 description 2
- 238000000199 molecular distillation Methods 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- KJRCEJOSASVSRA-UHFFFAOYSA-N propane-2-thiol Chemical compound CC(C)S KJRCEJOSASVSRA-UHFFFAOYSA-N 0.000 description 2
- 150000003254 radicals Chemical group 0.000 description 2
- 230000007017 scission Effects 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000004753 textile Substances 0.000 description 2
- UVMTZTPUIFOAGM-UHFFFAOYSA-N (3-chlorophenyl)carbamic acid Chemical compound OC(=O)NC1=CC=CC(Cl)=C1 UVMTZTPUIFOAGM-UHFFFAOYSA-N 0.000 description 1
- OQURWGJAWSLGQG-UHFFFAOYSA-N 1-isocyanatopropane Chemical compound CCCN=C=O OQURWGJAWSLGQG-UHFFFAOYSA-N 0.000 description 1
- GSLTVFIVJMCNBH-UHFFFAOYSA-N 2-isocyanatopropane Chemical compound CC(C)N=C=O GSLTVFIVJMCNBH-UHFFFAOYSA-N 0.000 description 1
- IBWUIERTVATGCO-UHFFFAOYSA-N 2-methylpropyl n-ethylcarbamate Chemical compound CCNC(=O)OCC(C)C IBWUIERTVATGCO-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- LXEPVHXXBMDAQC-UHFFFAOYSA-N OOOOOOOOOOOOOOOOOOOOOOOOOOO Chemical compound OOOOOOOOOOOOOOOOOOOOOOOOOOO LXEPVHXXBMDAQC-UHFFFAOYSA-N 0.000 description 1
- RRTCJVBFMMTZSS-UHFFFAOYSA-N SSSSSSSSSSSSS Chemical compound SSSSSSSSSSSSS RRTCJVBFMMTZSS-UHFFFAOYSA-N 0.000 description 1
- WOZQBERUBLYCEG-UHFFFAOYSA-N SWEP Chemical compound COC(=O)NC1=CC=C(Cl)C(Cl)=C1 WOZQBERUBLYCEG-UHFFFAOYSA-N 0.000 description 1
- 241001530097 Verbascum Species 0.000 description 1
- 235000010599 Verbascum thapsus Nutrition 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000003855 acyl compounds Chemical class 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- CSOLJDWYEPDGKF-UHFFFAOYSA-N benzyl n-propylcarbamate Chemical compound CCCNC(=O)OCC1=CC=CC=C1 CSOLJDWYEPDGKF-UHFFFAOYSA-N 0.000 description 1
- NRDQFWXVTPZZAZ-UHFFFAOYSA-N butyl carbonochloridate Chemical compound CCCCOC(Cl)=O NRDQFWXVTPZZAZ-UHFFFAOYSA-N 0.000 description 1
- FKCNTKCVNXZGGY-UHFFFAOYSA-N butyl n-nonylcarbamate Chemical compound CCCCCCCCCNC(=O)OCCCC FKCNTKCVNXZGGY-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 150000001715 carbamic acids Chemical class 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
- 238000007265 chloromethylation reaction Methods 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 125000000392 cycloalkenyl group Chemical group 0.000 description 1
- HNJIWFOWNMUNOP-UHFFFAOYSA-N cyclohexyl n-propylcarbamate Chemical compound CCCNC(=O)OC1CCCCC1 HNJIWFOWNMUNOP-UHFFFAOYSA-N 0.000 description 1
- ZAVUHLXZFYNAMG-UHFFFAOYSA-N ethyl n-cyclohexylcarbamate Chemical compound CCOC(=O)NC1CCCCC1 ZAVUHLXZFYNAMG-UHFFFAOYSA-N 0.000 description 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- RHGACTQWKOOOFE-UHFFFAOYSA-N methyl n-(2-chloroethyl)carbamate Chemical compound COC(=O)NCCCl RHGACTQWKOOOFE-UHFFFAOYSA-N 0.000 description 1
- SJTVPRCAJODHGA-UHFFFAOYSA-N methyl n-(2-chlorophenyl)carbamate Chemical compound COC(=O)NC1=CC=CC=C1Cl SJTVPRCAJODHGA-UHFFFAOYSA-N 0.000 description 1
- VIAYKPRGTANQHW-UHFFFAOYSA-N methyl n-(chloromethyl)-n-methylcarbamate Chemical compound COC(=O)N(C)CCl VIAYKPRGTANQHW-UHFFFAOYSA-N 0.000 description 1
- FTNVYYWQTDSXJO-UHFFFAOYSA-N methyl n-heptylcarbamate Chemical compound CCCCCCCNC(=O)OC FTNVYYWQTDSXJO-UHFFFAOYSA-N 0.000 description 1
- WKLZMQAKPRPVGI-UHFFFAOYSA-N methyl n-naphthalen-2-ylcarbamate Chemical compound C1=CC=CC2=CC(NC(=O)OC)=CC=C21 WKLZMQAKPRPVGI-UHFFFAOYSA-N 0.000 description 1
- UFEJKYYYVXYMMS-UHFFFAOYSA-N methylcarbamic acid Chemical compound CNC(O)=O UFEJKYYYVXYMMS-UHFFFAOYSA-N 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- FWJOCWFRSGXNIZ-UHFFFAOYSA-N o-propan-2-yl n-propylcarbamothioate Chemical compound CCCNC(=S)OC(C)C FWJOCWFRSGXNIZ-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- FGOAGQOXCGVTAT-UHFFFAOYSA-N propan-2-yl n-propylcarbamate Chemical compound CCCNC(=O)OC(C)C FGOAGQOXCGVTAT-UHFFFAOYSA-N 0.000 description 1
- VXPLXMJHHKHSOA-UHFFFAOYSA-N propham Chemical compound CC(C)OC(=O)NC1=CC=CC=C1 VXPLXMJHHKHSOA-UHFFFAOYSA-N 0.000 description 1
- POZHOUKVQOPXAJ-UHFFFAOYSA-N propyl n-propan-2-ylcarbamate Chemical compound CCCOC(=O)NC(C)C POZHOUKVQOPXAJ-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 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
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/86—Benzo [b] furans; Hydrogenated benzo [b] furans with an oxygen atom directly attached in position 7
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 |
|---|---|---|---|
| DE19712119518 DE2119518A1 (de) | 1971-04-22 | 1971-04-22 | Verfahren zur Herstellung von N-substituiertenN-Chlormethylcarbamidsäureestern und -thiolestern |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PL83653B1 true PL83653B1 (de) | 1975-12-31 |
Family
ID=5805461
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL1972154895A PL83653B1 (de) | 1971-04-22 | 1972-04-21 |
Country Status (12)
| Country | Link |
|---|---|
| AT (1) | AT317242B (de) |
| BE (1) | BE782383A (de) |
| CH (1) | CH566971A5 (de) |
| DD (1) | DD98513A5 (de) |
| DE (1) | DE2119518A1 (de) |
| FR (1) | FR2136602A5 (de) |
| GB (1) | GB1350528A (de) |
| HU (1) | HU164706B (de) |
| IL (1) | IL39246A (de) |
| IT (1) | IT957202B (de) |
| NL (1) | NL7205271A (de) |
| PL (1) | PL83653B1 (de) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2854599A1 (de) * | 1978-12-18 | 1980-06-26 | Basf Ag | Substituierte n-halogenmethylanilide und verfahren zu ihrer herstellung und verwendung |
| DE4237617A1 (de) * | 1992-11-06 | 1994-05-11 | Bayer Ag | Verwendung von substituierten Benzimidazolen |
| DE19642529A1 (de) | 1996-10-15 | 1998-04-16 | Bayer Ag | Aminophenolderivate |
| DE19831985A1 (de) | 1998-07-16 | 2000-01-20 | Bayer Ag | Substituierte Benzimidazole, ihre Herstellung und ihre Verwendung als Mittel gegen parasitäre Protozoen |
| TWI730297B (zh) * | 2018-02-27 | 2021-06-11 | 日商組合化學工業股份有限公司 | 巰基酚化合物的製造方法及巰基酚化合物的中間體 |
-
1971
- 1971-04-22 DE DE19712119518 patent/DE2119518A1/de active Pending
-
1972
- 1972-04-18 IL IL7239246A patent/IL39246A/en unknown
- 1972-04-19 NL NL7205271A patent/NL7205271A/xx unknown
- 1972-04-20 BE BE782383A patent/BE782383A/xx unknown
- 1972-04-20 CH CH587472A patent/CH566971A5/xx not_active IP Right Cessation
- 1972-04-20 IT IT7286/72A patent/IT957202B/it active
- 1972-04-21 DD DD162494A patent/DD98513A5/xx unknown
- 1972-04-21 PL PL1972154895A patent/PL83653B1/pl unknown
- 1972-04-21 HU HUBA2736A patent/HU164706B/hu unknown
- 1972-04-21 GB GB1861072A patent/GB1350528A/en not_active Expired
- 1972-04-21 FR FR7214228A patent/FR2136602A5/fr not_active Expired
- 1972-04-21 AT AT352172A patent/AT317242B/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| DD98513A5 (de) | 1973-06-20 |
| AT317242B (de) | 1974-08-26 |
| SU443510A3 (ru) | 1974-09-15 |
| FR2136602A5 (de) | 1972-12-22 |
| CH566971A5 (de) | 1975-09-30 |
| DE2119518A1 (de) | 1972-10-26 |
| BE782383A (fr) | 1972-10-20 |
| HU164706B (de) | 1974-04-11 |
| IL39246A (en) | 1976-01-30 |
| IT957202B (it) | 1973-10-10 |
| IL39246A0 (en) | 1972-06-28 |
| NL7205271A (de) | 1972-10-24 |
| GB1350528A (en) | 1974-04-18 |
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