DE1121055B - Verfahren zur Herstellung von 3-Amino-1, 2, 3-benzotriazinonen-(4) - Google Patents
Verfahren zur Herstellung von 3-Amino-1, 2, 3-benzotriazinonen-(4)Info
- Publication number
- DE1121055B DE1121055B DEF31236A DEF0031236A DE1121055B DE 1121055 B DE1121055 B DE 1121055B DE F31236 A DEF31236 A DE F31236A DE F0031236 A DEF0031236 A DE F0031236A DE 1121055 B DE1121055 B DE 1121055B
- Authority
- DE
- Germany
- Prior art keywords
- acid
- amino
- found
- calculated
- recrystallized
- 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 8
- 238000002360 preparation method Methods 0.000 title claims description 4
- KLSJWNVTNUYHDU-UHFFFAOYSA-N Amitrole Chemical compound NC1=NC=NN1 KLSJWNVTNUYHDU-UHFFFAOYSA-N 0.000 title 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 claims description 10
- 229940042795 hydrazides for tuberculosis treatment Drugs 0.000 claims description 5
- 125000000623 heterocyclic group Chemical group 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 150000003920 1,2,4-triazines Chemical class 0.000 claims description 2
- 125000001931 aliphatic group Chemical group 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 150000000111 pentazines Chemical class 0.000 claims description 2
- 150000004905 tetrazines Chemical class 0.000 claims description 2
- MGZUQDHNBYYFGF-UHFFFAOYSA-N 3-amino-1,2,3-benzotriazin-4-one Chemical class C1=CC=C2C(=O)N(N)N=NC2=C1 MGZUQDHNBYYFGF-UHFFFAOYSA-N 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 8
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 8
- TXJUTRJFNRYTHH-UHFFFAOYSA-N 1h-3,1-benzoxazine-2,4-dione Chemical compound C1=CC=C2C(=O)OC(=O)NC2=C1 TXJUTRJFNRYTHH-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 5
- -1 3-substituted 4-oxo-3,4-dihydro-1,2,3-benzotriazines Chemical class 0.000 description 5
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 235000010288 sodium nitrite Nutrition 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 150000002429 hydrazines Chemical class 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- 239000000155 melt Substances 0.000 description 3
- CPJSUEIXXCENMM-UHFFFAOYSA-N phenacetin Chemical compound CCOC1=CC=C(NC(C)=O)C=C1 CPJSUEIXXCENMM-UHFFFAOYSA-N 0.000 description 3
- 238000006798 ring closing metathesis reaction Methods 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- RHUYHJGZWVXEHW-UHFFFAOYSA-N 1,1-Dimethyhydrazine Chemical compound CN(C)N RHUYHJGZWVXEHW-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- UGBKOURNNQREPE-UHFFFAOYSA-N azepan-1-amine Chemical compound NN1CCCCCC1 UGBKOURNNQREPE-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- MKQLBNJQQZRQJU-UHFFFAOYSA-N morpholin-4-amine Chemical compound NN1CCOCC1 MKQLBNJQQZRQJU-UHFFFAOYSA-N 0.000 description 2
- 229960003893 phenacetin Drugs 0.000 description 2
- LWMPFIOTEAXAGV-UHFFFAOYSA-N piperidin-1-amine Chemical compound NN1CCCCC1 LWMPFIOTEAXAGV-UHFFFAOYSA-N 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- NVBFHJWHLNUMCV-UHFFFAOYSA-N sulfamide Chemical compound NS(N)(=O)=O NVBFHJWHLNUMCV-UHFFFAOYSA-N 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- IAFSUZIBZMPMPK-UHFFFAOYSA-N thiomorpholin-4-amine Chemical compound NN1CCSCC1 IAFSUZIBZMPMPK-UHFFFAOYSA-N 0.000 description 2
- DIIIISSCIXVANO-UHFFFAOYSA-N 1,2-Dimethylhydrazine Chemical compound CNNC DIIIISSCIXVANO-UHFFFAOYSA-N 0.000 description 1
- DMSSTTLDFWKBSX-UHFFFAOYSA-N 1h-1,2,3-benzotriazin-4-one Chemical class C1=CC=C2C(=O)N=NNC2=C1 DMSSTTLDFWKBSX-UHFFFAOYSA-N 0.000 description 1
- QMNWYGTWTXOQTP-UHFFFAOYSA-N 1h-triazin-6-one Chemical class O=C1C=CN=NN1 QMNWYGTWTXOQTP-UHFFFAOYSA-N 0.000 description 1
- RGUMYKJCYVFUET-UHFFFAOYSA-N 2-hydrazinylethane-1,1-diol Chemical compound OC(CNN)O RGUMYKJCYVFUET-UHFFFAOYSA-N 0.000 description 1
- XFXOLBNQYFRSLQ-UHFFFAOYSA-N 3-amino-2-naphthoic acid Chemical compound C1=CC=C2C=C(C(O)=O)C(N)=CC2=C1 XFXOLBNQYFRSLQ-UHFFFAOYSA-N 0.000 description 1
- RJWLLQWLBMJCFD-UHFFFAOYSA-N 4-methylpiperazin-1-amine Chemical compound CN1CCN(N)CC1 RJWLLQWLBMJCFD-UHFFFAOYSA-N 0.000 description 1
- DXSMYDSFWCOSFM-UHFFFAOYSA-N 6-bromo-1h-3,1-benzoxazine-2,4-dione Chemical compound N1C(=O)OC(=O)C2=CC(Br)=CC=C21 DXSMYDSFWCOSFM-UHFFFAOYSA-N 0.000 description 1
- WWUBAHSWMPFIQZ-UHFFFAOYSA-N 6-nitro-1h-3,1-benzoxazine-2,4-dione Chemical compound N1C(=O)OC(=O)C2=CC([N+](=O)[O-])=CC=C21 WWUBAHSWMPFIQZ-UHFFFAOYSA-N 0.000 description 1
- 241000581650 Ivesia Species 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 1
- OJKRGBWOZPMVAE-UHFFFAOYSA-N O1CCN(CC1)N1N=NC2=C(C1=O)C=C(C=C2)Br Chemical compound O1CCN(CC1)N1N=NC2=C(C1=O)C=C(C=C2)Br OJKRGBWOZPMVAE-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000004947 alkyl aryl amino group Chemical group 0.000 description 1
- RQGNEYFWHWFECS-UHFFFAOYSA-N amino formate Chemical class NOC=O RQGNEYFWHWFECS-UHFFFAOYSA-N 0.000 description 1
- 230000000202 analgesic effect Effects 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- NHOWLEZFTHYCTP-UHFFFAOYSA-N benzylhydrazine Chemical compound NNCC1=CC=CC=C1 NHOWLEZFTHYCTP-UHFFFAOYSA-N 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 125000004663 dialkyl amino group Chemical group 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- DKAGJZJALZXOOV-UHFFFAOYSA-N hydrate;hydrochloride Chemical compound O.Cl DKAGJZJALZXOOV-UHFFFAOYSA-N 0.000 description 1
- 238000006698 hydrazinolysis reaction Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- MPSUGQWRVNRJEE-UHFFFAOYSA-N triazol-1-amine Chemical compound NN1C=CN=N1 MPSUGQWRVNRJEE-UHFFFAOYSA-N 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
- C07D253/00—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00
- C07D253/08—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00 condensed with carbocyclic rings or ring systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/22—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with hetero atoms directly attached to ring nitrogen atoms
- C07D295/28—Nitrogen atoms
- C07D295/30—Nitrogen atoms non-acylated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL264713D NL264713A (enrdf_load_stackoverflow) | 1960-05-14 | ||
| DEF31236A DE1121055B (de) | 1960-05-14 | 1960-05-14 | Verfahren zur Herstellung von 3-Amino-1, 2, 3-benzotriazinonen-(4) |
| CH477261A CH396920A (de) | 1960-05-14 | 1961-04-24 | Verfahren zur Herstellung von 3-Amino-1,2,3-benzotriazinonen-(4) |
| BE603702A BE603702A (fr) | 1960-05-14 | 1961-05-12 | Procédé de préparation de 3-amino-1,2,3-benzotriazinones-(4) |
| DK617161A DK106612C (da) | 1960-05-14 | 1961-05-12 | Fremgangsmåde til fremstilling af 3-amino-1,2,3-benzotriazinon-(4)-forbindelser. |
| GB1764161A GB965573A (en) | 1960-05-14 | 1961-05-15 | 3-aminobenzotriazinones-(4) and their preparation |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF31236A DE1121055B (de) | 1960-05-14 | 1960-05-14 | Verfahren zur Herstellung von 3-Amino-1, 2, 3-benzotriazinonen-(4) |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1121055B true DE1121055B (de) | 1962-01-04 |
Family
ID=7094099
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEF31236A Pending DE1121055B (de) | 1960-05-14 | 1960-05-14 | Verfahren zur Herstellung von 3-Amino-1, 2, 3-benzotriazinonen-(4) |
Country Status (6)
| Country | Link |
|---|---|
| BE (1) | BE603702A (enrdf_load_stackoverflow) |
| CH (1) | CH396920A (enrdf_load_stackoverflow) |
| DE (1) | DE1121055B (enrdf_load_stackoverflow) |
| DK (1) | DK106612C (enrdf_load_stackoverflow) |
| GB (1) | GB965573A (enrdf_load_stackoverflow) |
| NL (1) | NL264713A (enrdf_load_stackoverflow) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3163646A (en) * | 1964-12-29 | J-aminobenzotriazinones- |
-
0
- NL NL264713D patent/NL264713A/xx unknown
-
1960
- 1960-05-14 DE DEF31236A patent/DE1121055B/de active Pending
-
1961
- 1961-04-24 CH CH477261A patent/CH396920A/de unknown
- 1961-05-12 BE BE603702A patent/BE603702A/fr unknown
- 1961-05-12 DK DK617161A patent/DK106612C/da active
- 1961-05-15 GB GB1764161A patent/GB965573A/en not_active Expired
Non-Patent Citations (1)
| Title |
|---|
| None * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3163646A (en) * | 1964-12-29 | J-aminobenzotriazinones- |
Also Published As
| Publication number | Publication date |
|---|---|
| DK106612C (da) | 1967-02-27 |
| GB965573A (en) | 1964-07-29 |
| NL264713A (enrdf_load_stackoverflow) | |
| CH396920A (de) | 1965-08-15 |
| BE603702A (fr) | 1961-11-13 |
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