FR2348205A1 - Dibenzo (b,f)-1,4-oxazepine useful as tear gas - is prepd. by ketalisation of a nitro-phenoxy benzaldehyde, redn. and hydrolysis - Google Patents
Dibenzo (b,f)-1,4-oxazepine useful as tear gas - is prepd. by ketalisation of a nitro-phenoxy benzaldehyde, redn. and hydrolysisInfo
- Publication number
- FR2348205A1 FR2348205A1 FR7611111A FR7611111A FR2348205A1 FR 2348205 A1 FR2348205 A1 FR 2348205A1 FR 7611111 A FR7611111 A FR 7611111A FR 7611111 A FR7611111 A FR 7611111A FR 2348205 A1 FR2348205 A1 FR 2348205A1
- Authority
- FR
- France
- Prior art keywords
- ketalisation
- redn
- oxazepine
- dibenzo
- hydrolysis
- 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.)
- Granted
Links
- 230000007062 hydrolysis Effects 0.000 title abstract 2
- 238000006460 hydrolysis reaction Methods 0.000 title abstract 2
- IMACFCSSMIZSPP-UHFFFAOYSA-N phenacyl chloride Chemical compound ClCC(=O)C1=CC=CC=C1 IMACFCSSMIZSPP-UHFFFAOYSA-N 0.000 title abstract 2
- 239000003491 tear gas Substances 0.000 title abstract 2
- MJQHHXRMMHHAMN-UHFFFAOYSA-N 3-nitro-2-phenoxybenzaldehyde Chemical compound [O-][N+](=O)C1=CC=CC(C=O)=C1OC1=CC=CC=C1 MJQHHXRMMHHAMN-UHFFFAOYSA-N 0.000 title 1
- UZVGSSNIUNSOFA-UHFFFAOYSA-N dibenzofuran-1-carboxylic acid Chemical compound O1C2=CC=CC=C2C2=C1C=CC=C2C(=O)O UZVGSSNIUNSOFA-UHFFFAOYSA-N 0.000 title 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 abstract 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract 3
- 238000000034 method Methods 0.000 abstract 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 abstract 1
- 239000003377 acid catalyst Substances 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 239000003849 aromatic solvent Substances 0.000 abstract 1
- 150000002009 diols Chemical class 0.000 abstract 1
- 230000000694 effects Effects 0.000 abstract 1
- 229940093476 ethylene glycol Drugs 0.000 abstract 1
- -1 ethyleneglycol Chemical class 0.000 abstract 1
- 231100001261 hazardous Toxicity 0.000 abstract 1
- 230000002427 irreversible effect Effects 0.000 abstract 1
- 230000003902 lesion Effects 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
- 239000008096 xylene Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
- C07D317/14—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D317/18—Radicals substituted by singly bound oxygen or sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C201/00—Preparation of esters of nitric or nitrous acid or of compounds containing nitro or nitroso groups bound to a carbon skeleton
- C07C201/06—Preparation of nitro compounds
- C07C201/12—Preparation of nitro compounds by reactions not involving the formation of nitro groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C213/02—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reactions involving the formation of amino groups from compounds containing hydroxy groups or etherified or esterified hydroxy groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D267/00—Heterocyclic compounds containing rings of more than six members having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D267/02—Seven-membered rings
- C07D267/08—Seven-membered rings having the hetero atoms in positions 1 and 4
- C07D267/12—Seven-membered rings having the hetero atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems
- C07D267/16—Seven-membered rings having the hetero atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems condensed with two six-membered rings
- C07D267/20—[b, f]-condensed
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Prepn. of dibenzo b,f. -1,4-oxazepine by (a) ketalisation of 2-(21-nitrophenoxy)-benzaldehyde using a 1-6C alkandiol or a 1-6C alkyl orthoformate; (b) redn. of the 21-nitroketal to the corresp. 21 amino-ketal and (c) hydrolysis of the 21-amino-ketal to the desired prod. Step (a) is pref. effected using the diol, e.g. ethyleneglycol, with an acid catalyst in an aromatic solvent with azeotropic distn. of water, esp. using benzene, toluene or xylene. Used as a tear-gas for maintaining public order, having a wide safety margin, limited sec. effects, good dispersing qualities, high stability and does not cause irreversible lesions. The known method of prodn. is hazardous and gives poor or variable yields. The present process gives better yields of sufficiently high purity.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7611111A FR2348205A1 (en) | 1976-04-15 | 1976-04-15 | Dibenzo (b,f)-1,4-oxazepine useful as tear gas - is prepd. by ketalisation of a nitro-phenoxy benzaldehyde, redn. and hydrolysis |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7611111A FR2348205A1 (en) | 1976-04-15 | 1976-04-15 | Dibenzo (b,f)-1,4-oxazepine useful as tear gas - is prepd. by ketalisation of a nitro-phenoxy benzaldehyde, redn. and hydrolysis |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FR2348205A1 true FR2348205A1 (en) | 1977-11-10 |
| FR2348205B1 FR2348205B1 (en) | 1978-08-25 |
Family
ID=9171875
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR7611111A Granted FR2348205A1 (en) | 1976-04-15 | 1976-04-15 | Dibenzo (b,f)-1,4-oxazepine useful as tear gas - is prepd. by ketalisation of a nitro-phenoxy benzaldehyde, redn. and hydrolysis |
Country Status (1)
| Country | Link |
|---|---|
| FR (1) | FR2348205A1 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0409412A2 (en) * | 1989-07-18 | 1991-01-23 | Imperial Chemical Industries Plc | Diaryl ether cyclic ethers |
-
1976
- 1976-04-15 FR FR7611111A patent/FR2348205A1/en active Granted
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0409412A2 (en) * | 1989-07-18 | 1991-01-23 | Imperial Chemical Industries Plc | Diaryl ether cyclic ethers |
| EP0409412A3 (en) * | 1989-07-18 | 1991-07-24 | Imperial Chemical Industries Plc | Diaryl ether cyclic ethers |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2348205B1 (en) | 1978-08-25 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| IE43752L (en) | A process for the manufacture of o-hydroxyaryl aldehydes | |
| IE791339L (en) | Derivatives of 19-nor-3,20-diketosteroids | |
| FR2348205A1 (en) | Dibenzo (b,f)-1,4-oxazepine useful as tear gas - is prepd. by ketalisation of a nitro-phenoxy benzaldehyde, redn. and hydrolysis | |
| AT367053B (en) | METHOD FOR THE PRODUCTION OF NEW AZULMIN ACIDS STABILIZED AGAINST CYAN HYDROGEN RELEASE | |
| JPS5549351A (en) | Preparation of aromatic primary hydroperoxide | |
| JPS5553265A (en) | Preparation of aromatic hydroperoxide | |
| ATE55382T1 (en) | PROCESS FOR THE PREPARATION OF OPTICALLY ACTIVE HYDROQUINONE DERIVATIVES AND D-ALPHATOCOPHEROL. | |
| JPS52131544A (en) | Phenoxymalonic acid derivatives and herbicides containing them | |
| IE40187L (en) | Pyrogen-free sub-unit vaccine. | |
| JPS5653131A (en) | Preparation of poly-vinylphenol | |
| ATE9991T1 (en) | PROCESS FOR PRODUCTION OF METHACRYLIC ACID FROM ISOBUTYRALDEHYDE. | |
| JPS5550473A (en) | Production of ketones | |
| JPS5273804A (en) | Production of ethylalcohol | |
| IE801910L (en) | Pyrogallol compounds | |
| GB1465512A (en) | 2-2-methyl-1-propen-1-yl-1,3-dioxans useful as perfumes | |
| JPS5282774A (en) | Decomposition of polyesters | |
| JPS52133912A (en) | Preparation of butanediol | |
| JPS5240483A (en) | Process for dialysis of acid | |
| JPS5325504A (en) | Isolation of glycols | |
| JPS5566534A (en) | Novel cyclic ketone compound and its preparation | |
| JPS55136240A (en) | Preparation of sesquiterpene derivative | |
| JPS55136285A (en) | Sesquiterpene derivative and its preparation | |
| JPS5525808A (en) | Manufacture of magnetic bubble element | |
| JPS55153781A (en) | Sesquiterpene derivative compound | |
| JPS51118548A (en) | Method of producing an outer blade of an electric razor |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| ST | Notification of lapse |