DE2211647A1 - Verfahren zur herstellung von 7-chlor1-methyl-5-phenyl-2,3-dihydro-1h-1,4benzodiazepin-2-on - Google Patents
Verfahren zur herstellung von 7-chlor1-methyl-5-phenyl-2,3-dihydro-1h-1,4benzodiazepin-2-onInfo
- Publication number
- DE2211647A1 DE2211647A1 DE19722211647 DE2211647A DE2211647A1 DE 2211647 A1 DE2211647 A1 DE 2211647A1 DE 19722211647 DE19722211647 DE 19722211647 DE 2211647 A DE2211647 A DE 2211647A DE 2211647 A1 DE2211647 A1 DE 2211647A1
- Authority
- DE
- Germany
- Prior art keywords
- methyl
- chloro
- phenyl
- preparation
- dihydro
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 6
- 238000002360 preparation method Methods 0.000 title claims description 5
- AAOVKJBEBIDNHE-UHFFFAOYSA-N diazepam Chemical compound N=1CC(=O)N(C)C2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 AAOVKJBEBIDNHE-UHFFFAOYSA-N 0.000 title 1
- 239000011541 reaction mixture Substances 0.000 claims description 4
- 238000010992 reflux Methods 0.000 claims description 4
- MWRWFPQBGSZWNV-UHFFFAOYSA-N Dinitrosopentamethylenetetramine Chemical compound C1N2CN(N=O)CN1CN(N=O)C2 MWRWFPQBGSZWNV-UHFFFAOYSA-N 0.000 claims description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 3
- 238000007363 ring formation reaction Methods 0.000 claims description 3
- CPLWKNRPZVNELG-UHFFFAOYSA-N (3-chlorophenyl)-phenylmethanone Chemical compound ClC1=CC=CC(C(=O)C=2C=CC=CC=2)=C1 CPLWKNRPZVNELG-UHFFFAOYSA-N 0.000 claims description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 239000003960 organic solvent Substances 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 20
- 150000001875 compounds Chemical class 0.000 description 11
- 239000003208 petroleum Substances 0.000 description 4
- 239000002249 anxiolytic agent Substances 0.000 description 2
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- UDLAUVFRZXIQJS-UHFFFAOYSA-N 1,3-dihydro-1,4-benzodiazepin-2-one Chemical compound N1C(=O)CN=CC2=CC=CC=C21 UDLAUVFRZXIQJS-UHFFFAOYSA-N 0.000 description 1
- ZXVONLUNISGICL-UHFFFAOYSA-N 4,6-dinitro-o-cresol Chemical group CC1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1O ZXVONLUNISGICL-UHFFFAOYSA-N 0.000 description 1
- IVUAAOBNUNMJQC-UHFFFAOYSA-N 5-phenyl-1,3-dihydro-1,4-benzodiazepin-2-one Chemical compound C12=CC=CC=C2NC(=O)CN=C1C1=CC=CC=C1 IVUAAOBNUNMJQC-UHFFFAOYSA-N 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- 230000000949 anxiolytic effect Effects 0.000 description 1
- 230000001914 calming effect Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000003158 myorelaxant agent Substances 0.000 description 1
- ATRGENZZRLPDFV-UHFFFAOYSA-N n-(2-benzoyl-4-chlorophenyl)-2-bromo-n-methylacetamide Chemical compound BrCC(=O)N(C)C1=CC=C(Cl)C=C1C(=O)C1=CC=CC=C1 ATRGENZZRLPDFV-UHFFFAOYSA-N 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 230000000069 prophylactic effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 230000004799 sedative–hypnotic effect Effects 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D243/00—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms
- C07D243/06—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4
- C07D243/10—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems
- C07D243/14—1,4-Benzodiazepines; Hydrogenated 1,4-benzodiazepines
- C07D243/16—1,4-Benzodiazepines; Hydrogenated 1,4-benzodiazepines substituted in position 5 by aryl radicals
- C07D243/18—1,4-Benzodiazepines; Hydrogenated 1,4-benzodiazepines substituted in position 5 by aryl radicals substituted in position 2 by nitrogen, oxygen or sulfur atoms
- C07D243/24—Oxygen atoms
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 |
|---|---|---|---|
| YU63471A YU63471A (en) | 1971-03-15 | 1971-03-15 | Process for preparing 7-chloro-1-methyl-5-phenyl-2,3-dihydro-1h-1,4-benzodiazepin-2-ones |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2211647A1 true DE2211647A1 (de) | 1973-08-09 |
Family
ID=25550780
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19722211647 Pending DE2211647A1 (de) | 1971-03-15 | 1972-03-10 | Verfahren zur herstellung von 7-chlor1-methyl-5-phenyl-2,3-dihydro-1h-1,4benzodiazepin-2-on |
Country Status (10)
| Country | Link |
|---|---|
| JP (1) | JPS5239039B1 (enExample) |
| AT (1) | AT316558B (enExample) |
| BE (1) | BE780591A (enExample) |
| CH (1) | CH567487A5 (enExample) |
| DE (1) | DE2211647A1 (enExample) |
| DK (1) | DK134433B (enExample) |
| EG (1) | EG10623A (enExample) |
| FR (1) | FR2130148B1 (enExample) |
| GB (1) | GB1338365A (enExample) |
| YU (1) | YU63471A (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS52106881A (en) * | 1976-03-05 | 1977-09-07 | Crc Ricerca Chim | Production of 1*44 benzodiazepine derivative |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1343475A (fr) * | 1960-12-09 | 1963-11-22 | Hoffmann La Roche | Procédé de préparation de dérivés de 1, 4-benzodiazéipne |
-
1971
- 1971-03-15 YU YU63471A patent/YU63471A/xx unknown
-
1972
- 1972-03-07 EG EG8772A patent/EG10623A/xx active
- 1972-03-08 AT AT192172A patent/AT316558B/de not_active IP Right Cessation
- 1972-03-09 GB GB1117472A patent/GB1338365A/en not_active Expired
- 1972-03-10 DE DE19722211647 patent/DE2211647A1/de active Pending
- 1972-03-10 FR FR7208363A patent/FR2130148B1/fr not_active Expired
- 1972-03-13 BE BE780591A patent/BE780591A/xx unknown
- 1972-03-14 CH CH370772A patent/CH567487A5/xx not_active IP Right Cessation
- 1972-03-14 JP JP47025320A patent/JPS5239039B1/ja active Pending
- 1972-03-14 DK DK116972A patent/DK134433B/da unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS52106881A (en) * | 1976-03-05 | 1977-09-07 | Crc Ricerca Chim | Production of 1*44 benzodiazepine derivative |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5239039B1 (enExample) | 1977-10-03 |
| DK134433C (enExample) | 1981-03-30 |
| EG10623A (en) | 1976-04-30 |
| YU63471A (en) | 1978-10-31 |
| CH567487A5 (enExample) | 1975-10-15 |
| DK134433B (da) | 1976-11-08 |
| FR2130148A1 (enExample) | 1972-11-03 |
| AT316558B (de) | 1974-07-25 |
| GB1338365A (en) | 1973-11-21 |
| BE780591A (fr) | 1972-07-03 |
| FR2130148B1 (enExample) | 1977-01-14 |
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