DD159637A5 - Acylierungsmittel zur acylierung von phenolischen hydroxylgruppen - Google Patents
Acylierungsmittel zur acylierung von phenolischen hydroxylgruppen Download PDFInfo
- Publication number
- DD159637A5 DD159637A5 DD23091580A DD23091580A DD159637A5 DD 159637 A5 DD159637 A5 DD 159637A5 DD 23091580 A DD23091580 A DD 23091580A DD 23091580 A DD23091580 A DD 23091580A DD 159637 A5 DD159637 A5 DD 159637A5
- Authority
- DD
- German Democratic Republic
- Prior art keywords
- acylating agent
- carbon atoms
- sulfimide
- base
- group
- Prior art date
Links
- -1 HYDROXYL GROUPS Chemical group 0.000 title claims abstract description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims abstract description 32
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 22
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 14
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 9
- 230000010933 acylation Effects 0.000 claims abstract description 7
- 238000005917 acylation reaction Methods 0.000 claims abstract description 7
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims abstract description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 6
- 239000002904 solvent Substances 0.000 claims abstract description 6
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 4
- 229940081974 saccharin Drugs 0.000 claims abstract 2
- 235000019204 saccharin Nutrition 0.000 claims abstract 2
- 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 claims abstract 2
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 36
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 125000003944 tolyl group Chemical group 0.000 claims 1
- 239000002253 acid Substances 0.000 abstract description 3
- 238000002360 preparation method Methods 0.000 abstract description 3
- MLEVBPIRDRGCQE-UHFFFAOYSA-N [SH2]=N.CC1=C(C=CC=C1)NC(=O)C1=C(C(=O)O)C=CC=C1 Chemical compound [SH2]=N.CC1=C(C=CC=C1)NC(=O)C1=C(C(=O)O)C=CC=C1 MLEVBPIRDRGCQE-UHFFFAOYSA-N 0.000 abstract description 2
- BSCCSDNZEIHXOK-UHFFFAOYSA-N phenyl carbamate Chemical class NC(=O)OC1=CC=CC=C1 BSCCSDNZEIHXOK-UHFFFAOYSA-N 0.000 abstract description 2
- 239000011814 protection agent Substances 0.000 abstract description 2
- 125000002252 acyl group Chemical group 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- 239000000203 mixture Substances 0.000 description 14
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- 150000001875 compounds Chemical class 0.000 description 10
- 239000000155 melt Substances 0.000 description 10
- 239000012948 isocyanate Substances 0.000 description 8
- 150000002513 isocyanates Chemical class 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- 239000002585 base Substances 0.000 description 5
- 239000012153 distilled water Substances 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- 239000012452 mother liquor Substances 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 239000000284 extract Substances 0.000 description 3
- FFQQCJGNKKIRMD-UHFFFAOYSA-N methyl n-(3-hydroxyphenyl)carbamate Chemical compound COC(=O)NC1=CC=CC(O)=C1 FFQQCJGNKKIRMD-UHFFFAOYSA-N 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- WJGPNUBJBMCRQH-UHFFFAOYSA-N 2,2-dimethyl-2,3-dihydro-1-benzofuran-7-ol Chemical compound C1=CC(O)=C2OC(C)(C)CC2=C1 WJGPNUBJBMCRQH-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 2
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 2
- OLDRZWKGXUGNOW-UHFFFAOYSA-N [SH2]=N.CNC(=O)C1=CC=CC=C1C(O)=O Chemical compound [SH2]=N.CNC(=O)C1=CC=CC=C1C(O)=O OLDRZWKGXUGNOW-UHFFFAOYSA-N 0.000 description 2
- DUEPRVBVGDRKAG-UHFFFAOYSA-N carbofuran Chemical compound CNC(=O)OC1=CC=CC2=C1OC(C)(C)C2 DUEPRVBVGDRKAG-UHFFFAOYSA-N 0.000 description 2
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 2
- 230000008030 elimination Effects 0.000 description 2
- 238000003379 elimination reaction Methods 0.000 description 2
- LHGVFZTZFXWLCP-UHFFFAOYSA-N guaiacol Chemical compound COC1=CC=CC=C1O LHGVFZTZFXWLCP-UHFFFAOYSA-N 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 2
- 231100000331 toxic Toxicity 0.000 description 2
- 230000002588 toxic effect Effects 0.000 description 2
- ZAGNMMRDHSEOPE-UHFFFAOYSA-N (2-chlorophenyl) n-methylcarbamate Chemical compound CNC(=O)OC1=CC=CC=C1Cl ZAGNMMRDHSEOPE-UHFFFAOYSA-N 0.000 description 1
- OTYKXVWEKXHDHH-UHFFFAOYSA-N (2-methoxyphenyl) n-methylcarbamate Chemical compound CNC(=O)OC1=CC=CC=C1OC OTYKXVWEKXHDHH-UHFFFAOYSA-N 0.000 description 1
- ODIGIKRIUKFKHP-UHFFFAOYSA-N (n-propan-2-yloxycarbonylanilino) acetate Chemical compound CC(C)OC(=O)N(OC(C)=O)C1=CC=CC=C1 ODIGIKRIUKFKHP-UHFFFAOYSA-N 0.000 description 1
- QCGCZQXNAUVPKJ-UHFFFAOYSA-N 2-(4-hydroxy-5-methoxycyclohexa-2,4-dien-1-ylidene)acetonitrile Chemical compound COC1=C(O)C=CC(=CC#N)C1 QCGCZQXNAUVPKJ-UHFFFAOYSA-N 0.000 description 1
- ISPYQTSUDJAMAB-UHFFFAOYSA-N 2-chlorophenol Chemical compound OC1=CC=CC=C1Cl ISPYQTSUDJAMAB-UHFFFAOYSA-N 0.000 description 1
- SNUSVOJPWBPLEF-UHFFFAOYSA-N [SH2]=N.CC1=CC=CC(NC(=O)C=2C(=CC=CC=2)C(O)=O)=C1 Chemical compound [SH2]=N.CC1=CC=CC(NC(=O)C=2C(=CC=CC=2)C(O)=O)=C1 SNUSVOJPWBPLEF-UHFFFAOYSA-N 0.000 description 1
- VHKREQQTTZHFAC-UHFFFAOYSA-N [SH2]=N.CCCCNC(=O)C1=CC=CC=C1C(O)=O Chemical compound [SH2]=N.CCCCNC(=O)C1=CC=CC=C1C(O)=O VHKREQQTTZHFAC-UHFFFAOYSA-N 0.000 description 1
- HHCTWXMZENAHIE-UHFFFAOYSA-N [SH2]=N.CCCCNC(O)=O.OC(=O)C1=CC=CC=C1 Chemical compound [SH2]=N.CCCCNC(O)=O.OC(=O)C1=CC=CC=C1 HHCTWXMZENAHIE-UHFFFAOYSA-N 0.000 description 1
- 238000003916 acid precipitation Methods 0.000 description 1
- 125000004442 acylamino group Chemical group 0.000 description 1
- 238000007259 addition reaction Methods 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- AOGYCOYQMAVAFD-UHFFFAOYSA-N chlorocarbonic acid Chemical class OC(Cl)=O AOGYCOYQMAVAFD-UHFFFAOYSA-N 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- KCLZXXMMEDEBMF-UHFFFAOYSA-N ethyl n-(3-hydroxyphenyl)carbamate Chemical compound CCOC(=O)NC1=CC=CC(O)=C1 KCLZXXMMEDEBMF-UHFFFAOYSA-N 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 229960001867 guaiacol Drugs 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 210000004400 mucous membrane Anatomy 0.000 description 1
- 230000000269 nucleophilic effect Effects 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003512 tertiary amines Chemical class 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)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HUCI001984 HU184063B (en) | 1979-11-08 | 1979-11-08 | Process for producing carbamoic-acid-phenyl-ester derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DD159637A5 true DD159637A5 (de) | 1983-03-23 |
Family
ID=10994773
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD23091580A DD159637A5 (de) | 1979-11-08 | 1980-11-05 | Acylierungsmittel zur acylierung von phenolischen hydroxylgruppen |
| DD22498880A DD154100A5 (de) | 1979-11-08 | 1980-11-05 | Verfahren zur herstellung von carbaminsaeureester-derivaten durch o-acylierung |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD22498880A DD154100A5 (de) | 1979-11-08 | 1980-11-05 | Verfahren zur herstellung von carbaminsaeureester-derivaten durch o-acylierung |
Country Status (10)
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HU185294B (en) * | 1980-12-29 | 1984-12-28 | Chinoin Gyogyszer Es Vegyeszet | Process for producing substituted urea derivatives |
| FR2612186B1 (fr) * | 1987-03-09 | 1989-07-21 | Poudres & Explosifs Ste Nale | Carbonyl 2,2' bis (alkyl-4 oxadiazolidines-1,2,4-diones-3,5), leur procede de preparation et leur utilisation comme intermediaires de synthese dans la preparation de carbamates |
| IE62527B1 (en) * | 1987-06-25 | 1995-02-08 | Lilly Co Eli | Process for preparing ureas |
| JP4821680B2 (ja) * | 2007-03-30 | 2011-11-24 | 大日本印刷株式会社 | 塩基増殖剤、それを用いた樹脂組成物、及び物品 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE792313A (fr) * | 1971-12-06 | 1973-03-30 | Quimco Gmbh | Procede de preparation de carbamates mono substitues sur l'atome d'azote et produits obtenus |
| HU167249B (enrdf_load_stackoverflow) * | 1973-04-24 | 1975-09-27 |
-
1979
- 1979-11-08 HU HUCI001984 patent/HU184063B/hu unknown
-
1980
- 1980-10-29 DE DE19803040633 patent/DE3040633A1/de active Granted
- 1980-11-04 CS CS744780A patent/CS219932B2/cs unknown
- 1980-11-04 YU YU280880A patent/YU280880A/xx unknown
- 1980-11-04 PL PL22765180A patent/PL127976B1/pl unknown
- 1980-11-05 FR FR8023596A patent/FR2469399A1/fr active Granted
- 1980-11-05 DD DD23091580A patent/DD159637A5/de not_active IP Right Cessation
- 1980-11-05 JP JP15476980A patent/JPS5683461A/ja active Pending
- 1980-11-05 DD DD22498880A patent/DD154100A5/de not_active IP Right Cessation
- 1980-11-05 SU SU803003801A patent/SU1176833A3/ru active
- 1980-11-06 GB GB8035667A patent/GB2065639B/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5683461A (en) | 1981-07-08 |
| GB2065639B (en) | 1983-10-26 |
| DD154100A5 (de) | 1982-02-24 |
| SU1176833A3 (ru) | 1985-08-30 |
| YU280880A (en) | 1983-12-31 |
| FR2469399B1 (enrdf_load_stackoverflow) | 1984-05-11 |
| DE3040633C2 (enrdf_load_stackoverflow) | 1989-01-05 |
| FR2469399A1 (fr) | 1981-05-22 |
| GB2065639A (en) | 1981-07-01 |
| CS219932B2 (en) | 1983-03-25 |
| DE3040633A1 (de) | 1981-05-21 |
| PL127976B1 (en) | 1983-12-31 |
| PL227651A1 (enrdf_load_stackoverflow) | 1981-08-21 |
| HU184063B (en) | 1984-06-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| ENJ | Ceased due to non-payment of renewal fee |