US2302162A - Process for producing guanamine derivatives - Google Patents
Process for producing guanamine derivatives Download PDFInfo
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- US2302162A US2302162A US388984A US38898441A US2302162A US 2302162 A US2302162 A US 2302162A US 388984 A US388984 A US 388984A US 38898441 A US38898441 A US 38898441A US 2302162 A US2302162 A US 2302162A
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- piperidine
- guanamine derivatives
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
Definitions
- Our present invention relates to an improved process for producing guanamine derivatives of the general formula:
- R stands for a member of the group consisting of an alkyl and the benzyl radicle
- the present improved process consists in heating a mixture of dicyandiamide, a nitrile cor'npound of the formula RCN, wherein R has the aforesaid significance, and a strongly basiccompound.
- reaction is advantageously carried out in a closed vessel.
- Example 1 A mixture of 84 parts of dicyandiamide, 250
- piperidine instead of piperidine corresponding amounts of other compounds of a strongly basic character such as diethylenetriamine, pyrrolidine, tetrahydroquinoline or' potassium carbonate or so- A dium hydroxide maybe added.
- Example 3 A mixture of 300 parts of ,B-naphthohitrile, 84 parts of dicyandiamide, 3.to 5 parts of piperidine (or pyrrolidine or henzylamine) is heated. while stirring at 200 to 205 for 3 to 4 hours. When cool the reaction mass is diluted with an organic solvent of a low boiling point such as carbon tetrachloride and the precipitate is filtered oil. The 4.6-dlamino-2-(2'-naphthyl) -triazine oi the iormula N thus obtained is a white powder having a melting point of 240 C. It is soluble in high boill5 ing solvents such as benzonitrile. The yield is the theoretical whereas without the addition of a basic agent there is obtained a substantially smaller yield of a product of an inaccurate melting point and only partly soluble in benzonitrile.
- Example 4 A mixture of 84 parts of dicyandiamide, 250 parts of benzylcyanide and about 8 parts of piperidine is heated to boiling for about 3 hours. 4.6-diamino-2-benzyl-triazine-1.3.5 of the formula:
- R stands for a member of the group consisting of an alkyl and the benzyl radicle, an aromatic radicle of the benzene and naphthalene series and a heterocyclic radicle of the iurane series which consists in heating a mixture of dicyanamide, a nitrile compound of the formula RCN, wherein R has the aforesaid significance, and a strongly basic compound.
Description
Patented Nov. 17, 1942 UNITED I STATES PATENT. OFFICE 2,302,162 raocsss ron. rnonvomc GUANAMINE nnarvs'rrvns Werner Zerweck and Walter Brenner, Frankfort-- on-the-Main-Fechenheim, Germany; vested in the Alien Property Oustpdlan No Drawing. Application April 17, 1941, Serial No. 388,984. In Germany May 9, 1940 7 Claims.
Our present invention relates to an improved process for producing guanamine derivatives of the general formula:
wherein R stands for a member of the group consisting of an alkyl and the benzyl radicle,
an "aromatic radicle of the benzene-and naphthalene series and a heterocyclic 'radicle of the furane series.
The present improved process consists in heating a mixture of dicyandiamide, a nitrile cor'npound of the formula RCN, wherein R has the aforesaid significance, and a strongly basiccompound.
When using nitrile compounds of a relatively low boiling point the reaction is advantageously carried out in a closed vessel.
Whereas the hitherto known processes convert following examples are given, the parts being by weight and all temperatures in degrees centigrade.
Example 1 A mixture of 84 parts of dicyandiamide, 250
parts of acetonitrile and 16 parts of piperidine is heated for about 5 hours at about 190 to 195 in an autoclave. The crystallizing reaction product is 4.6-diaminoQ-methyltriazin-1.3.5 (acetoguanamine) EH2 fi HzN-C $-CH1 The product has a melting point of 263 c. The yield obtained surpasses. 80% of the theoretical, whereas without the addition of a basic compound such as piperidine there is obtained an impure reaction product melting at 200 to 216 C. in a yield of about 60% of the theoretical. When adding 10 parts of ethylene-diamine instead of piperidine to the reaction mixture, a similar good result is obtained.
When replacing the acetonitrile by the equivalent amount of propionitrile, the 4.6-diamino- 2-ethyltriazine-l.3.5 is obtained.
Example? A mixture of 84.p arts of dicyandiamide, 250
parts of benzonitrile and about 8 parts of piperidine isheated for about 3 hours almostto the boiling point of the benzonitrile. 4.6-diamino- 2-phenyltriazine-1.3.5 (benzoguanamine) of the I formula:
crystallizes from the solution when pool. This product has a melting point of 222 and is-obtained in a yield of 85% of the throretical, whereas without the addition ofpiperidine only a product containing about per cent of melamine is obtained in a yield of about 40% of the theoretical.
The same result is obtained when heating to boiling a mixtureof 42 parts-of dicyandiamide, parts of benzonitrile, about parts of diethylbenzene and 4 parts of piperidine for about 3 hours. a
Instead of piperidine corresponding amounts of other compounds of a strongly basic character such as diethylenetriamine, pyrrolidine, tetrahydroquinoline or' potassium carbonate or so- A dium hydroxide maybe added.
When'replacingthe: benzonitrile by the equivalent amount of the'three isomeric chlorobenzonitriles or methylbenzonitriles the corresponding substitution products of vbenzoguanamine are obtained bearing, a chlorine atom or a methyl group .in the ortho-, metaor para-position of the benzene 'nucleus standing in the 2-position of the triazine ring.
Example 3 A mixture of 300 parts of ,B-naphthohitrile, 84 parts of dicyandiamide, 3.to 5 parts of piperidine (or pyrrolidine or henzylamine) is heated. while stirring at 200 to 205 for 3 to 4 hours. When cool the reaction mass is diluted with an organic solvent of a low boiling point such as carbon tetrachloride and the precipitate is filtered oil. The 4.6-dlamino-2-(2'-naphthyl) -triazine oi the iormula N thus obtained is a white powder having a melting point of 240 C. It is soluble in high boill5 ing solvents such as benzonitrile. The yield is the theoretical whereas without the addition of a basic agent there is obtained a substantially smaller yield of a product of an inaccurate melting point and only partly soluble in benzonitrile.
Example 4 A mixture of 84 parts of dicyandiamide, 250 parts of benzylcyanide and about 8 parts of piperidine is heated to boiling for about 3 hours. 4.6-diamino-2-benzyl-triazine-1.3.5 of the formula:
is obtained. The same is a colorless powder melting at 248- 250 0., soluble in hot water and scarcely soluble in alcohol and benzene.
We claim:
1. Improved process for producing guanamine derivatives of the general formula:
wherein R stands for a member of the group consisting of an alkyl and the benzyl radicle, an aromatic radicle of the benzene and naphthalene series and a heterocyclic radicle of the iurane series which consists in heating a mixture of dicyanamide, a nitrile compound of the formula RCN, wherein R has the aforesaid significance, and a strongly basic compound.
2. The process as defined in claim 1 wherein R is alkyl.
3. The process as defined in claim 1 wherein 'R is alkyl and wherein the strongly basic compound is a heterocyclic compound.
4. The process as defined in claim' 1 wherein R. is methyl and the strongly basic compound is piperidine.
5. The process as defined in claim 1 wherein R is an aryl of the benzene series.
6. The process as defined in claim 1 wherein R is phenyl and the strongly basic compound is piperidlne.
7. The process as defined in claim 1 wherein R is naphthyl and the strongly basic compound is piperidine. V
WERNER ZERWECK. WALTER BRUNNER.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2302162X | 1940-05-09 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2302162A true US2302162A (en) | 1942-11-17 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US388984A Expired - Lifetime US2302162A (en) | 1940-05-09 | 1941-04-17 | Process for producing guanamine derivatives |
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| US (1) | US2302162A (en) |
Cited By (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2463471A (en) * | 1949-03-01 | Halogen-substituted guanamines | ||
| US2491658A (en) * | 1949-12-20 | Guanamines | ||
| US2532519A (en) * | 1950-12-05 | diguanamines | ||
| US2535968A (en) * | 1945-04-13 | 1950-12-26 | American Cyanamid Co | Heterocyclic guanamines |
| US2548772A (en) * | 1951-04-10 | Method of preparing cyanobutyl | ||
| US2606904A (en) * | 1952-08-12 | Preparation of guanamines | ||
| US2619486A (en) * | 1952-11-25 | Dialkoxyacetoguanamines | ||
| US2761779A (en) * | 1952-04-29 | 1956-09-04 | American Cyanamid Co | Method of making pulp pre-forms and products thereof |
| US2832779A (en) * | 1955-03-30 | 1958-04-29 | Basf Ag | Production of 4-aryl-2.6-dihydroxy-1.3.5-triazines |
| US3157651A (en) * | 1964-11-17 | Triazine compounds | ||
| US3259627A (en) * | 1963-02-18 | 1966-07-05 | Ciba Ltd | Furyl and thienyl hydroxyaryl-1, 3, 5-triazines |
| US3352861A (en) * | 1965-12-15 | 1967-11-14 | Velsicol Chemical Corp | Process for the recovery of acetoguanamine |
| CN102731420A (en) * | 2012-06-26 | 2012-10-17 | 四川金象赛瑞化工股份有限公司 | Method for preparing acetoguanamine |
-
1941
- 1941-04-17 US US388984A patent/US2302162A/en not_active Expired - Lifetime
Cited By (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3157651A (en) * | 1964-11-17 | Triazine compounds | ||
| US2619486A (en) * | 1952-11-25 | Dialkoxyacetoguanamines | ||
| US2532519A (en) * | 1950-12-05 | diguanamines | ||
| US2463471A (en) * | 1949-03-01 | Halogen-substituted guanamines | ||
| US2548772A (en) * | 1951-04-10 | Method of preparing cyanobutyl | ||
| US2606904A (en) * | 1952-08-12 | Preparation of guanamines | ||
| US2491658A (en) * | 1949-12-20 | Guanamines | ||
| US2535968A (en) * | 1945-04-13 | 1950-12-26 | American Cyanamid Co | Heterocyclic guanamines |
| US2761779A (en) * | 1952-04-29 | 1956-09-04 | American Cyanamid Co | Method of making pulp pre-forms and products thereof |
| US2832779A (en) * | 1955-03-30 | 1958-04-29 | Basf Ag | Production of 4-aryl-2.6-dihydroxy-1.3.5-triazines |
| US3259627A (en) * | 1963-02-18 | 1966-07-05 | Ciba Ltd | Furyl and thienyl hydroxyaryl-1, 3, 5-triazines |
| US3352861A (en) * | 1965-12-15 | 1967-11-14 | Velsicol Chemical Corp | Process for the recovery of acetoguanamine |
| CN102731420A (en) * | 2012-06-26 | 2012-10-17 | 四川金象赛瑞化工股份有限公司 | Method for preparing acetoguanamine |
| CN102731420B (en) * | 2012-06-26 | 2015-02-04 | 四川金象赛瑞化工股份有限公司 | Method for preparing acetoguanamine |
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