http://rdf.ncbi.nlm.nih.gov/pubchem/patent/GB-759396-A
Outgoing Links
| Predicate | Object |
|---|---|
| assignee | http://rdf.ncbi.nlm.nih.gov/pubchem/patentassignee/MD5_653f5c196338bcb4c8f94debd09cdaad |
| classificationCPCInventive | http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07F9-657154 |
| classificationIPCInventive | http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07F9-6571 |
| filingDate | 1954-02-22-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| publicationDate | 1956-10-17-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| publicationNumber | GB-759396-A |
| titleOfInvention | Heterocyclic phosphorus-containing compounds and the production thereof |
| abstract | The invention comprises amido derivatives of heterocyclic phosphorus-containing compounds having the formula <FORM:0759396/IV(a)/1> wherein R, R1, R2, R3 and R4 represent a hydrogen atom or an alkyl radical; R5 and R6 represent a hydrogen atom or an alkyl, aralkyl, cyanoalkyl, alkaryl, monocyclic aryl or haloaryl radical, or together represent the atoms necessary to complete a morpholinyl or a piperidinyl ring; n is 1 or 0. The novel compounds are prepared by reacting a compound having a HN= group, such as ammonia, or a primary or secondary alkyl, aralkyl, or cyanoalkyl amine, an aryl, alkaryl or haloaryl amine, or a heterocyclic amine such as morpholine or piperidine, with the corresponding 2-halo-2-oxa-1,3,2-dioxaphospholane or 2-halo-2-oxo-1,3,2-dioxaphosphorinane. The halogen atom may be chlorine, bromine or iodine. Suitable amines are mono- and di-methyl, ethyl, butyl, octyl, heptadecyl, 2-cyanoethylphenyl, cresyl, benzyl, p - chlorophenyl or o - bromophenyl amines. Reaction temperatures between - 30 DEG C. and 130 DEG C., preferably 10 DEG C. to 80 DEG C., may be used, and the reaction may be effected in the presence of a hydrogen halide sequestering agent, e.g. pyridine, and a volatile inert solvent such as ethyl ether. Numerous examples of the process are given, typical products being 2-amido - 5 - ethyl - 4 - propyl -, 2 - di - isopropylamido - 5 - ethyl - 4 - propyl -, 4 - methyl - 2-morpholido -, 2[di(21cyanoethyl)amido] - 5-ethyl - 4 - propyl -, 2(p - chlorophenylamido)-5,5 - diethyl - and 5 - ethyl - 4 - propyl - 2-piperidido - derivatives of 2 - oxo - 1,3,2 - dioxahphosphorinane and 2 - dibutylamido - 4-methyl - 2 - oxo - 1,3,2 - dioxaphospholane. The 2 - halo - 2 - oxo - 1,3,2 - dioxaphosphorinanes and the corresponding 1,3,2-dioxaphospholanes may be prepared by reacting a phosphoryl halide, such as the chloride or bromide, with a 1,2- or 1,3-alkanediol, such as 1,2-propanediol or 1,3-hexanediol, preferably in the presence of a hydrogen halide sequestering agent and an inert solvent for the reactant. The reaction is preferably conducted at temperatures of 50 DEG C. or below, more preferably - 10 DEG C. to 25 DEG C. Detailed examples are given of the preparation of 2-chloro-4-methyl-2-oxo-1,3,2-dioxaphospholane and 2-chloro-5-ethyl-4-propyl - 2 - oxo - 1,3,2 - dioxaphosphorinane from phosphoryl chloride with 1,2-propanediol and 2-ethyl - 1,3 - hexanediol respectively. Other suitable diols are 2,3- and 2,4-pentanediols, 2-butyl - 2 - ethyl - 1,3 - propanediol, 2,2 - diethyl - 1,3 - propanediol, 2 - methyl - 2,4 - pentanediol, 1,3- and 2,3-butanediols, 1,3-isopentanediol, 1,2-isobutanediol and 2,3-pentanediol. The 2-halo-starting material may also be prepared by reacting a 2-alkoxy-substituted1,3,2-dioxaphosphorinane or the corresponding dioxaphospholane with a halogen, such as chlorine, bromine or iodine, at a temperature between - 30 DEG C. and 50 DEG C. Detailed examples are given of the preparation of 2-bromo5 - butyl - 5 - ethyl - 2 - oxo - 1,3,2 - dioxaphosphorinane and 5 - butyl - 5 - ethyl - 2 - iodo - 2 - oxo - 1,3,2 - dioxaphosphorinane. |
| isCitedBy | http://rdf.ncbi.nlm.nih.gov/pubchem/patent/CN-102516302-A http://rdf.ncbi.nlm.nih.gov/pubchem/patent/US-3270093-A |
| priorityDate | 1953-03-04-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| type | http://data.epo.org/linked-data/def/patent/Publication |
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