GB777546A - Improvements relating to substituted iminodibenzyls - Google Patents
Improvements relating to substituted iminodibenzylsInfo
- Publication number
- GB777546A GB777546A GB26973/55A GB2697355A GB777546A GB 777546 A GB777546 A GB 777546A GB 26973/55 A GB26973/55 A GB 26973/55A GB 2697355 A GB2697355 A GB 2697355A GB 777546 A GB777546 A GB 777546A
- Authority
- GB
- United Kingdom
- Prior art keywords
- substituted
- dichloro
- diphosphate
- diamino
- nitro
- 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.)
- Expired
Links
- 239000001177 diphosphate Substances 0.000 abstract 3
- 235000011180 diphosphates Nutrition 0.000 abstract 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 abstract 2
- 229960003116 amyl nitrite Drugs 0.000 abstract 2
- -1 chloro-substituted 2-nitro-toluene Chemical class 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- XPPKVPWEQAFLFU-UHFFFAOYSA-J diphosphate(4-) Chemical compound [O-]P([O-])(=O)OP([O-])([O-])=O XPPKVPWEQAFLFU-UHFFFAOYSA-J 0.000 abstract 2
- 238000010438 heat treatment Methods 0.000 abstract 2
- CSDTZUBPSYWZDX-UHFFFAOYSA-N n-pentyl nitrite Chemical compound CCCCCON=O CSDTZUBPSYWZDX-UHFFFAOYSA-N 0.000 abstract 2
- 229920000137 polyphosphoric acid Polymers 0.000 abstract 2
- XCSNRORTQRKCHB-UHFFFAOYSA-N 2-chloro-6-nitrotoluene Chemical compound CC1=C(Cl)C=CC=C1[N+]([O-])=O XCSNRORTQRKCHB-UHFFFAOYSA-N 0.000 abstract 1
- SQFLFRQWPBEDHM-UHFFFAOYSA-N 4-chloro-1-methyl-2-nitrobenzene Chemical compound CC1=CC=C(Cl)C=C1[N+]([O-])=O SQFLFRQWPBEDHM-UHFFFAOYSA-N 0.000 abstract 1
- 239000007868 Raney catalyst Substances 0.000 abstract 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 abstract 1
- 229910000564 Raney nickel Inorganic materials 0.000 abstract 1
- 125000003963 dichloro group Chemical group Cl* 0.000 abstract 1
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- 230000003647 oxidation Effects 0.000 abstract 1
- 238000007254 oxidation reaction Methods 0.000 abstract 1
- 235000011007 phosphoric acid Nutrition 0.000 abstract 1
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 abstract 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 abstract 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention comprises compounds of the formula: <FORM:0777546/IV(b)/1> Such compounds are obtained by heating a disubstituted 2.21-diaminodibenzyl of the formula: <FORM:0777546/IV(b)/2> or the diphosphate thereof with polyphosphoric acid at 220 DEG to 300 DEG C. Dichloro substituted 2.21 - diamino - dibenzyls are obtained by oxidation of chloro-substituted 2-nitro-toluene, e.g. with amyl nitrite, to form the corresponding dihalogen - substituted 2.21 - dinitrodibenzyls, which is then catalytically hydrogenated. In examples: (1) 2-nitro-4-chlorotoluene is treated in ether with amyl nitrite in the presence of sodium ethoxide to give 2.21-dinitro-4.41-dichlorodibenzyl which is hydrogenated using Raney nickel to 2.21-diamino-4.41-dichlorbenzyl. The latter is converted to the diphosphate which on heating with polyphosphoric acid (from orthophosphoric acid and phosphorus pentoxide) gives 3.7-dichloro-iminodibenzyl; (2) from 6-chloro-2-nitro-toluene, 1.9-dichloroiminodibenzyl is prepared, 2.2-dinitro-6.61-dichloro - dibenzyl and 2.21 - diamino - 6.61-dichloro-dibenzyl diphosphate being formed as intermediates.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH777546X | 1954-09-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB777546A true GB777546A (en) | 1957-06-26 |
Family
ID=4535936
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB26973/55A Expired GB777546A (en) | 1954-09-22 | 1955-09-21 | Improvements relating to substituted iminodibenzyls |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB777546A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7663001B2 (en) | 1998-05-11 | 2010-02-16 | Basf Aktiengesellschaft | Preparation of isoxazolin-3-ylacylbenzene |
-
1955
- 1955-09-21 GB GB26973/55A patent/GB777546A/en not_active Expired
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7663001B2 (en) | 1998-05-11 | 2010-02-16 | Basf Aktiengesellschaft | Preparation of isoxazolin-3-ylacylbenzene |
| US8049017B2 (en) | 1998-05-11 | 2011-11-01 | Basf Se | Preparation of isoxazolin-3-ylacylbenzenes |
| US8124810B2 (en) | 1998-05-11 | 2012-02-28 | Basf Se | Preparation of isoxazolin-3-ylacylbenzenes |
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