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Reply
| | | From: jchemie (Original Message) | Sent: 4/20/2006 9:12 PM |
Hello Friends, I am synthesizing 4 nitroimino perhydro 1,3,5 oxadiazine. I wanted
to know what are the properties of 4-nitroimino perhydro oxadiazine.
Coiuld anyone tell me its MP, and appearance. Also please tell me what
it the exact proceedure to prepare it from nitroguanidine. I have tried
using acid catalysis but fot a product melting to a sticky material at
room temperature. Please help me with it. Waiting for your reply.
Thanks
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Jyot Vakharia
www.sitesonthespot.com
info@sitesontespot.com |
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| | From:  ·Steve· | Sent: 4/20/2006 11:35 PM |
I don't have an immediate reference to the properties of 4-nitroimino-perhydro-1,3,5-oxadiazine. Possibly it could be prepared from the reaction of bis(chloromethyl) ether with nitroguanidine? Problem with that is that the nitro group in nitroguanidine is not on the imino nitrogen. Steve |
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| | | From: jchemie | Sent: 4/21/2006 1:04 PM |
Hi steve, Have already synthesized using formaldehyde condensation in acidic media. But dont know the props so cannot guess if the compound is proper or not. Please get the rfrences if you can get. Thanks Jyot Vakharia www.sitesonthespot.com |
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Reply
| | | From: ·Steve· | Sent: 4/22/2006 10:40 PM |
Just wanted to verify that this is the structure of 4-nitroimino-perhydro-1,3,5-oxadiazine:
O
/ \
H2C CH2
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HN NH
\ /
C
�?BR> N
\
NO2
Molecular formula = C3H6N4O3. Do you have access to a library where you can do a Chemical Abstracts search? If the synthesis by the condensation reaction of nitroguanidine with formaldehyde is an established procedure, it's just a matter of finding it in the chemical literature. Good luck!
Steve
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| | | From: jchemie | Sent: 4/23/2006 10:22 AM |
Well the structure you guessed was right. I am getting the product my the proceedure but it is not stable. SO i need the property. Please help!1 jyot Vakharia |
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Reply
| | | From: ·Steve· | Sent: 4/23/2006 8:13 PM |
The 3-methyl derivative 3-methyl-4-nitroimino-perhydro-1,3,5-oxadiazine, CAS #153719-38-1, seems to be a stable solid and a common pesticide ingredient. If you could convert your supposed 4-nitroimino-perhydro-1,3,5-oxadiazine to a known derivative such as this by reaction with an alkyl halide, that would indicate that you do indeed have the correct precursor. But substitution may occur preferentially at the 5 position if the 3 position is more hindered by the nitro group.
Does a literature search on 4-nitroimino-perhydro-1,3,5-oxadiazine turn up anything? I mean a search through Chem Abstracts, for example, that's the only way to get reliable information. If you don't have access to a good university library, you're in a tough spot. Given the competitive nature of the field (pesticide chemistry) I would imagine such information would not be volunteered very freely on the Internet, except by guys like me that have no vested interest and unfortunately not much useful info to share on the subject either!
I find your project to be a very interesting one, and very challenging given the complexities of the reactions involved. As you say, the compound may be inherently unstable, which would explain the lack of direct references.
Steve
A few links, mainly for my own reference; I'm sure you know these works very well!
The Pesticide Manual, 10th Edition (1994), The British Crop Protection Council, London
(Cited frequently in the patent descriptions.)
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Reply
| | | From: ·Steve· | Sent: 4/24/2006 3:05 PM |
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Interesting document - A challenge to a claim of the synthesis of 4-nitroimino-perhydro-1,3,5-oxadiazine as an intermediate or byproduct in a related reaction. The experimental procedure is given on p. 11:
"Example 5 specifically states that: A mixture consisting of nitroguanidine (10 g), methoxyamine hydrochloride (9.6 g), 75% paraformaldehyde (11.5 g), toluene (80 ml) and a catalytic amount of concentrated hydrochloric acid was subjected to heating under reflux for three hours, while the water was removed therefrom.[2] Under reduced pressure, the solvent contained in the mixture was distilled off to obtain white crystals of the hydrochloride of 5-methoxy-2-nitroimino-hexahydro-1,3,5-triazine (16.2 g) having a melting point from 160° to 170°C."
The reaction forming 4-nitroimino-perhydro-1,3,5-oxadiazine is given on p. 42.
It was claimed that:
"A person of ordinary skill in the art of heterocyclic chemistry in the 1988-90 time frame knew that production of 1,3,5-oxadiazines could occur without any external nucleophile like water. Only the formaldehyde, a guanidine, and an acidic environment are needed. 1,3,5-oxadiazines have been synthesized under non-aqueous conditions (from a urea, paraformaldehyde with an acid catalyst in chloroform) by Seidel et al. SX 2052."
But this claim was challenged:
"Example 5 makes no mention as to the coproduction of a 1,3,5-oxadiazine intermediate compound. ..."
This case was heard by the Board of Patent Appeals in 2001. It looks like, up to that time, there was not an actual published procedure using "only the formaldehyde, a guanidine, and an acidic environment" to prepare the oxadiazine, or it would have been referred to specifically.
Steve
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