DE2530521B2 - Verfahren zur Herstellung von N-(Carbamoyl-oxy-phenyO-carbaminsäureestern - Google Patents
Verfahren zur Herstellung von N-(Carbamoyl-oxy-phenyO-carbaminsäureesternInfo
- Publication number
- DE2530521B2 DE2530521B2 DE2530521A DE2530521A DE2530521B2 DE 2530521 B2 DE2530521 B2 DE 2530521B2 DE 2530521 A DE2530521 A DE 2530521A DE 2530521 A DE2530521 A DE 2530521A DE 2530521 B2 DE2530521 B2 DE 2530521B2
- Authority
- DE
- Germany
- Prior art keywords
- carbamic acid
- ecm
- ester
- mol
- phenyl
- 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.)
- Ceased
Links
- 238000000034 method Methods 0.000 title claims description 22
- 238000002360 preparation method Methods 0.000 title claims description 8
- 229940112021 centrally acting muscle relaxants carbamic acid ester Drugs 0.000 title description 3
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 238000005809 transesterification reaction Methods 0.000 claims description 4
- AURJXZJUNOGUEO-UHFFFAOYSA-N (2-carbamoyloxyphenyl)carbamic acid Chemical class NC(=O)OC1=CC=CC=C1NC(O)=O AURJXZJUNOGUEO-UHFFFAOYSA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 36
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 33
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 21
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 18
- 239000000047 product Substances 0.000 description 14
- 239000011541 reaction mixture Substances 0.000 description 12
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 5
- -1 monochlorophenyl Chemical group 0.000 description 5
- WQEBQCOHDAWORA-UHFFFAOYSA-N (2,3,4,5,6-pentachlorophenyl) n-phenylcarbamate Chemical compound ClC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1OC(=O)NC1=CC=CC=C1 WQEBQCOHDAWORA-UHFFFAOYSA-N 0.000 description 4
- 239000004480 active ingredient Substances 0.000 description 4
- FFQQCJGNKKIRMD-UHFFFAOYSA-N methyl n-(3-hydroxyphenyl)carbamate Chemical compound COC(=O)NC1=CC=CC(O)=C1 FFQQCJGNKKIRMD-UHFFFAOYSA-N 0.000 description 4
- 238000006467 substitution reaction Methods 0.000 description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 125000000753 cycloalkyl group Chemical group 0.000 description 3
- KCLZXXMMEDEBMF-UHFFFAOYSA-N ethyl n-(3-hydroxyphenyl)carbamate Chemical compound CCOC(=O)NC1=CC=CC(O)=C1 KCLZXXMMEDEBMF-UHFFFAOYSA-N 0.000 description 3
- SIZKDIQMNFWPBD-UHFFFAOYSA-N hydroxy(phenyl)carbamic acid Chemical compound OC(=O)N(O)C1=CC=CC=C1 SIZKDIQMNFWPBD-UHFFFAOYSA-N 0.000 description 3
- 239000012948 isocyanate Substances 0.000 description 3
- 150000002513 isocyanates Chemical class 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- CKDWPUIZGOQOOM-UHFFFAOYSA-N Carbamyl chloride Chemical compound NC(Cl)=O CKDWPUIZGOQOOM-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 238000005917 acylation reaction Methods 0.000 description 2
- 238000007259 addition reaction Methods 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 150000007529 inorganic bases Chemical class 0.000 description 2
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- IZUPBVBPLAPZRR-UHFFFAOYSA-N pentachlorophenol Chemical compound OC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl IZUPBVBPLAPZRR-UHFFFAOYSA-N 0.000 description 2
- 239000012429 reaction media Substances 0.000 description 2
- 230000008929 regeneration Effects 0.000 description 2
- 238000011069 regeneration method Methods 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 150000003512 tertiary amines Chemical class 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- WFTJCZOBXDNNOZ-UHFFFAOYSA-N (2,3,4,5,6-pentachlorophenyl) N-cyclohexylcarbamate Chemical compound ClC1=C(C(=C(C(=C1OC(NC1CCCCC1)=O)Cl)Cl)Cl)Cl WFTJCZOBXDNNOZ-UHFFFAOYSA-N 0.000 description 1
- WIOWJWLWAPTJDR-UHFFFAOYSA-N (2,3,4,5,6-pentachlorophenyl) n-(3-chlorophenyl)carbamate Chemical compound ClC1=CC=CC(NC(=O)OC=2C(=C(Cl)C(Cl)=C(Cl)C=2Cl)Cl)=C1 WIOWJWLWAPTJDR-UHFFFAOYSA-N 0.000 description 1
- GMEYMTDUKUVNKW-UHFFFAOYSA-N (2,3,4,5,6-pentachlorophenyl) n-(3-methylphenyl)carbamate Chemical compound CC1=CC=CC(NC(=O)OC=2C(=C(Cl)C(Cl)=C(Cl)C=2Cl)Cl)=C1 GMEYMTDUKUVNKW-UHFFFAOYSA-N 0.000 description 1
- GIPHFLWHNAYKHC-UHFFFAOYSA-N (2,3,4,5,6-pentachlorophenyl) n-(4-chlorophenyl)carbamate Chemical compound C1=CC(Cl)=CC=C1NC(=O)OC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl GIPHFLWHNAYKHC-UHFFFAOYSA-N 0.000 description 1
- FTCSFJOFZGYXFX-UHFFFAOYSA-N (2,3,4,5,6-pentachlorophenyl) n-methylcarbamate Chemical compound CNC(=O)OC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl FTCSFJOFZGYXFX-UHFFFAOYSA-N 0.000 description 1
- NMELKTWAMSTJPD-UHFFFAOYSA-N (2-hydroxyphenyl)carbamic acid Chemical compound OC(=O)NC1=CC=CC=C1O NMELKTWAMSTJPD-UHFFFAOYSA-N 0.000 description 1
- LCEYJTJDZROKOK-UHFFFAOYSA-N (3-hydroxyphenyl)carbamic acid Chemical compound OC(=O)NC1=CC=CC(O)=C1 LCEYJTJDZROKOK-UHFFFAOYSA-N 0.000 description 1
- HNAXBZUMENBWSX-UHFFFAOYSA-N (3-methylphenyl)carbamic acid Chemical compound CC1=CC=CC(NC(O)=O)=C1 HNAXBZUMENBWSX-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 230000006181 N-acylation Effects 0.000 description 1
- 125000005118 N-alkylcarbamoyl group Chemical group 0.000 description 1
- 230000006179 O-acylation Effects 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 125000005037 alkyl phenyl group Chemical group 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 230000002252 carbamoylating effect Effects 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000013078 crystal Substances 0.000 description 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 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 125000004464 hydroxyphenyl group Chemical group 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 230000021962 pH elevation Effects 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- BSCCSDNZEIHXOK-UHFFFAOYSA-N phenyl carbamate Chemical compound NC(=O)OC1=CC=CC=C1 BSCCSDNZEIHXOK-UHFFFAOYSA-N 0.000 description 1
- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 1
- 235000020004 porter Nutrition 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 102000012498 secondary active transmembrane transporter activity proteins Human genes 0.000 description 1
- 108040003878 secondary active transmembrane transporter activity proteins Proteins 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000001544 thienyl 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
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
- C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
- C07C271/26—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atom of at least one of the carbamate groups bound to a carbon atom of a six-membered aromatic ring
- C07C271/28—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atom of at least one of the carbamate groups bound to a carbon atom of a six-membered aromatic ring to a carbon atom of a non-condensed six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C269/00—Preparation of derivatives of carbamic acid, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C269/00—Preparation of derivatives of carbamic acid, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C269/04—Preparation of derivatives of carbamic acid, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups from amines with formation of carbamate groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
- C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
- C07C271/10—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C271/12—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
- C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
- C07C271/10—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C271/16—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of hydrocarbon radicals substituted by singly-bound oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
- C07C271/40—Esters of carbamic acids having oxygen atoms of carbamate groups bound to carbon atoms of six-membered aromatic rings
- C07C271/42—Esters of carbamic acids having oxygen atoms of carbamate groups bound to carbon atoms of six-membered aromatic rings with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C271/44—Esters of carbamic acids having oxygen atoms of carbamate groups bound to carbon atoms of six-membered aromatic rings with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HUCI1490A HU170115B (enrdf_load_html_response) | 1974-07-12 | 1974-07-12 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2530521A1 DE2530521A1 (de) | 1976-01-29 |
| DE2530521B2 true DE2530521B2 (de) | 1978-03-16 |
Family
ID=10994526
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2530521A Ceased DE2530521B2 (de) | 1974-07-12 | 1975-07-09 | Verfahren zur Herstellung von N-(Carbamoyl-oxy-phenyO-carbaminsäureestern |
Country Status (23)
-
1974
- 1974-07-12 HU HUCI1490A patent/HU170115B/hu unknown
-
1975
- 1975-07-08 IL IL47668A patent/IL47668A/xx unknown
- 1975-07-09 EG EG401/75A patent/EG11800A/xx active
- 1975-07-09 DE DE2530521A patent/DE2530521B2/de not_active Ceased
- 1975-07-10 SE SE7507951A patent/SE420088B/xx unknown
- 1975-07-10 NL NL7508245A patent/NL7508245A/xx not_active Application Discontinuation
- 1975-07-10 FR FR7521688A patent/FR2277816A1/fr active Granted
- 1975-07-10 IN IN1349/CAL/1975A patent/IN140842B/en unknown
- 1975-07-10 ES ES439294A patent/ES439294A1/es not_active Expired
- 1975-07-10 FI FI752008A patent/FI61873C/fi not_active IP Right Cessation
- 1975-07-11 DD DD187258A patent/DD121512A2/xx unknown
- 1975-07-11 CA CA231,284A patent/CA1064048A/en not_active Expired
- 1975-07-11 GB GB29290/75A patent/GB1479250A/en not_active Expired
- 1975-07-11 AR AR259528A patent/AR222621A1/es active
- 1975-07-11 DK DK318175AA patent/DK139027B/da not_active IP Right Cessation
- 1975-07-11 BE BE158200A patent/BE831262A/xx not_active IP Right Cessation
- 1975-07-11 CS CS754932A patent/CS194721B2/cs unknown
- 1975-07-11 SU SU752153655A patent/SU886738A3/ru active
- 1975-07-11 CH CH912775A patent/CH618584A5/de not_active IP Right Cessation
- 1975-07-11 NO NO752505A patent/NO752505L/no unknown
- 1975-07-11 JP JP50084566A patent/JPS5132542A/ja active Pending
- 1975-07-12 PL PL1975182043A patent/PL104534B1/pl unknown
- 1975-07-14 MX MX75100304U patent/MX3678E/es unknown
Also Published As
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8235 | Patent refused |