CS196409B2 - Process for preparing 4-phenyl-2/1h/quinazolinones - Google Patents
Process for preparing 4-phenyl-2/1h/quinazolinones Download PDFInfo
- Publication number
- CS196409B2 CS196409B2 CS778309A CS830977A CS196409B2 CS 196409 B2 CS196409 B2 CS 196409B2 CS 778309 A CS778309 A CS 778309A CS 830977 A CS830977 A CS 830977A CS 196409 B2 CS196409 B2 CS 196409B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- acid
- methyl
- trifluoromethyl
- phenyl
- temperatures
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title abstract description 3
- 238000000034 method Methods 0.000 claims abstract description 26
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims abstract description 24
- MAOBFOXLCJIFLV-UHFFFAOYSA-N (2-aminophenyl)-phenylmethanone Chemical compound NC1=CC=CC=C1C(=O)C1=CC=CC=C1 MAOBFOXLCJIFLV-UHFFFAOYSA-N 0.000 claims abstract description 8
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims abstract description 8
- 239000004202 carbamide Substances 0.000 claims abstract description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 150000001875 compounds Chemical class 0.000 claims description 10
- 239000005711 Benzoic acid Substances 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 8
- 235000010233 benzoic acid Nutrition 0.000 claims description 8
- GTCAXTIRRLKXRU-UHFFFAOYSA-N methyl carbamate Chemical compound COC(N)=O GTCAXTIRRLKXRU-UHFFFAOYSA-N 0.000 claims description 8
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 8
- -1 6,7-methylenedioxy Chemical group 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 5
- 125000004414 alkyl thio group Chemical group 0.000 claims description 4
- 125000001246 bromo group Chemical group Br* 0.000 claims description 4
- 125000001153 fluoro group Chemical group F* 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- LPNBBFKOUUSUDB-UHFFFAOYSA-N p-toluic acid Chemical compound CC1=CC=C(C(O)=O)C=C1 LPNBBFKOUUSUDB-UHFFFAOYSA-N 0.000 claims description 4
- 239000011541 reaction mixture Substances 0.000 claims description 4
- AVRPFRMDMNDIDH-UHFFFAOYSA-N 1h-quinazolin-2-one Chemical class C1=CC=CC2=NC(O)=NC=C21 AVRPFRMDMNDIDH-UHFFFAOYSA-N 0.000 claims description 3
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- JTIGKVIOEQASGT-UHFFFAOYSA-N proquazone Chemical compound N=1C(=O)N(C(C)C)C2=CC(C)=CC=C2C=1C1=CC=CC=C1 JTIGKVIOEQASGT-UHFFFAOYSA-N 0.000 claims description 3
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- ZWLPBLYKEWSWPD-UHFFFAOYSA-N o-toluic acid Chemical compound CC1=CC=CC=C1C(O)=O ZWLPBLYKEWSWPD-UHFFFAOYSA-N 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- OECSGKJNSQDODP-UHFFFAOYSA-N 1,4-dihydroquinoline-2,3-dione Chemical compound C1=CC=C2NC(=O)C(=O)CC2=C1 OECSGKJNSQDODP-UHFFFAOYSA-N 0.000 claims 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims 1
- FHUBTSLLILWICW-UHFFFAOYSA-N 4-phenyl-1h-quinazolin-2-one Chemical class C12=CC=CC=C2NC(=O)N=C1C1=CC=CC=C1 FHUBTSLLILWICW-UHFFFAOYSA-N 0.000 abstract description 4
- 229940121363 anti-inflammatory agent Drugs 0.000 abstract 1
- 239000002260 anti-inflammatory agent Substances 0.000 abstract 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 238000007363 ring formation reaction Methods 0.000 description 5
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- NTURVSFTOYPGON-UHFFFAOYSA-N Dihydroquinazoline Chemical class C1=CC=C2C=NCNC2=C1 NTURVSFTOYPGON-UHFFFAOYSA-N 0.000 description 2
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- HHTYFUMRSWVPQZ-UHFFFAOYSA-N 1-ethyl-6-nitro-4-phenylquinazolin-2-one Chemical compound N=1C(=O)N(CC)C2=CC=C([N+]([O-])=O)C=C2C=1C1=CC=CC=C1 HHTYFUMRSWVPQZ-UHFFFAOYSA-N 0.000 description 1
- WNTYZOYZMPPLTD-UHFFFAOYSA-N 1-methylquinazolin-2-one Chemical compound C1=CC=C2C=NC(=O)N(C)C2=C1 WNTYZOYZMPPLTD-UHFFFAOYSA-N 0.000 description 1
- IHXKXSJKLJZXKZ-UHFFFAOYSA-N 2-aminocyclohexa-2,5-diene-1,4-dione Chemical class NC1=CC(=O)C=CC1=O IHXKXSJKLJZXKZ-UHFFFAOYSA-N 0.000 description 1
- SWDKFBABKQQWOZ-UHFFFAOYSA-N 4-(2,6-dimethoxyphenyl)-1-methylquinazolin-2-one Chemical compound CN1C(N=C(C2=CC=CC=C12)C1=C(C=CC=C1OC)OC)=O SWDKFBABKQQWOZ-UHFFFAOYSA-N 0.000 description 1
- QGHJRJCNYBJPFL-UHFFFAOYSA-N 6-methoxy-4-phenyl-1-propan-2-ylquinazolin-2-one Chemical compound C12=CC(OC)=CC=C2N(C(C)C)C(=O)N=C1C1=CC=CC=C1 QGHJRJCNYBJPFL-UHFFFAOYSA-N 0.000 description 1
- ZCAZGTAWHVZVPE-UHFFFAOYSA-N 7-methylsulfanyl-4-phenyl-1-propan-2-ylquinazolin-2-one Chemical compound C(C)(C)N1C(N=C(C2=CC=C(C=C12)SC)C1=CC=CC=C1)=O ZCAZGTAWHVZVPE-UHFFFAOYSA-N 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 239000005557 antagonist Substances 0.000 description 1
- 159000000032 aromatic acids Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- WDIHJSXYQDMJHN-UHFFFAOYSA-L barium chloride Chemical compound [Cl-].[Cl-].[Ba+2] WDIHJSXYQDMJHN-UHFFFAOYSA-L 0.000 description 1
- 229910001626 barium chloride Inorganic materials 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 125000001207 fluorophenyl group Chemical group 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000007935 neutral effect Effects 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
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 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
- C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
- C07D239/72—Quinazolines; Hydrogenated quinazolines
- C07D239/78—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in position 2
- C07D239/80—Oxygen atoms
- C07D239/82—Oxygen atoms with an aryl radical attached in position 4
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1561976A CH625512A5 (fi) | 1976-12-13 | 1976-12-13 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS196409B2 true CS196409B2 (en) | 1980-03-31 |
Family
ID=4410585
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS778309A CS196409B2 (en) | 1976-12-13 | 1977-12-12 | Process for preparing 4-phenyl-2/1h/quinazolinones |
Country Status (31)
| Country | Link |
|---|---|
| US (1) | US4236006A (fi) |
| JP (1) | JPS5377077A (fi) |
| AR (1) | AR220526A1 (fi) |
| AT (1) | AT371450B (fi) |
| AU (1) | AU517193B2 (fi) |
| BE (1) | BE861775A (fi) |
| CA (1) | CA1091229A (fi) |
| CH (1) | CH625512A5 (fi) |
| CS (1) | CS196409B2 (fi) |
| DD (1) | DD133327A5 (fi) |
| DE (1) | DE2753970A1 (fi) |
| DK (1) | DK143025C (fi) |
| ES (1) | ES464966A1 (fi) |
| FI (1) | FI64358C (fi) |
| FR (1) | FR2373534A1 (fi) |
| GB (1) | GB1592687A (fi) |
| GR (1) | GR71667B (fi) |
| HU (1) | HU176875B (fi) |
| IE (1) | IE46492B1 (fi) |
| IL (1) | IL53588A (fi) |
| IT (1) | IT1090572B (fi) |
| NL (1) | NL7713651A (fi) |
| NO (1) | NO147484C (fi) |
| NZ (1) | NZ185933A (fi) |
| OA (1) | OA05821A (fi) |
| PH (1) | PH15458A (fi) |
| PT (1) | PT67388B (fi) |
| SE (1) | SE442996B (fi) |
| SU (1) | SU793391A3 (fi) |
| YU (1) | YU40687B (fi) |
| ZA (1) | ZA777425B (fi) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4617392A (en) * | 1983-09-29 | 1986-10-14 | Ortho Pharmaceutical Corporation | 4-alkyl-5,6-methylenedioxy-2-1[H]-quinazolinones useful as cardiotonic agents |
| AR038658A1 (es) * | 2001-06-15 | 2005-01-26 | Novartis Ag | Derivados de 4-aril-2(1h) quinazolinona y 4-aril-quinazolina 2-sustituidas, un proceso para su preparacion, composiciones farmaceuticas y el uso de dichos derivados para la preparacion de un medicamento |
| GB0230015D0 (en) * | 2002-12-23 | 2003-01-29 | Novartis Ag | Organic compounds |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3547921A (en) * | 1968-12-26 | 1970-12-15 | Sandoz Ag | Preparation of 1-substituted-4-aryl-3,4-dihydro-2(1h)-quinazolinones |
| US3642897A (en) * | 1968-12-26 | 1972-02-15 | Sandoz Ag | Preparation of 2-alkylaminobenzophenones |
| US3551427A (en) * | 1969-05-09 | 1970-12-29 | Sandoz Ag | 4-thienyl-2-(1h)-quinazolones |
| DK135044B (da) * | 1971-05-06 | 1977-02-28 | Sandoz Ag | Analogifremgangsmåde til fremstilling af 4-phenyl- eller 4-(2'-thienyl)-6,7-methylendioxy-2(1H)-quinazolinoner eller -2(1H)-quinazolinthioner. |
| BE790804A (fr) * | 1971-11-18 | 1973-04-30 | Sandoz Sa | Procede de preparation de derives de la quinazoline |
| CH580083A5 (en) * | 1973-04-03 | 1976-09-30 | Sumitomo Chemical Co | 4-Aryl-2-(1H)-quinazolinones prepn - by hydrolysis or thermolysis of 2-(acylureido)-benzophenones |
-
1976
- 1976-12-13 CH CH1561976A patent/CH625512A5/de not_active IP Right Cessation
-
1977
- 1977-12-02 FI FI773659A patent/FI64358C/fi not_active IP Right Cessation
- 1977-12-03 DE DE19772753970 patent/DE2753970A1/de not_active Withdrawn
- 1977-12-05 SE SE7713742A patent/SE442996B/sv not_active IP Right Cessation
- 1977-12-05 NO NO774147A patent/NO147484C/no unknown
- 1977-12-05 DK DK540877A patent/DK143025C/da not_active IP Right Cessation
- 1977-12-06 FR FR7736661A patent/FR2373534A1/fr active Granted
- 1977-12-08 GB GB51144/77A patent/GB1592687A/en not_active Expired
- 1977-12-09 CA CA292,750A patent/CA1091229A/en not_active Expired
- 1977-12-09 NL NL7713651A patent/NL7713651A/xx not_active Application Discontinuation
- 1977-12-10 GR GR54959A patent/GR71667B/el unknown
- 1977-12-12 HU HU77SA3080A patent/HU176875B/hu not_active IP Right Cessation
- 1977-12-12 JP JP14823077A patent/JPS5377077A/ja active Granted
- 1977-12-12 OA OA56337A patent/OA05821A/xx unknown
- 1977-12-12 BE BE183388A patent/BE861775A/xx not_active IP Right Cessation
- 1977-12-12 NZ NZ185933A patent/NZ185933A/xx unknown
- 1977-12-12 ES ES464966A patent/ES464966A1/es not_active Expired
- 1977-12-12 AR AR270333A patent/AR220526A1/es active
- 1977-12-12 PH PH20542A patent/PH15458A/en unknown
- 1977-12-12 IL IL53588A patent/IL53588A/xx unknown
- 1977-12-12 IE IE2518/77A patent/IE46492B1/en unknown
- 1977-12-12 PT PT67388A patent/PT67388B/pt unknown
- 1977-12-12 DD DD7700202556A patent/DD133327A5/xx unknown
- 1977-12-12 AT AT0884677A patent/AT371450B/de not_active IP Right Cessation
- 1977-12-12 AU AU31438/77A patent/AU517193B2/en not_active Expired
- 1977-12-12 CS CS778309A patent/CS196409B2/cs unknown
- 1977-12-12 SU SU772552353A patent/SU793391A3/ru active
- 1977-12-13 IT IT52191/77A patent/IT1090572B/it active
- 1977-12-13 ZA ZA00777425A patent/ZA777425B/xx unknown
- 1977-12-13 YU YU2945/77A patent/YU40687B/xx unknown
-
1979
- 1979-02-01 US US06/008,328 patent/US4236006A/en not_active Expired - Lifetime
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