IL43032A - The production of 6-azauracil - Google Patents
The production of 6-azauracilInfo
- Publication number
- IL43032A IL43032A IL43032A IL4303273A IL43032A IL 43032 A IL43032 A IL 43032A IL 43032 A IL43032 A IL 43032A IL 4303273 A IL4303273 A IL 4303273A IL 43032 A IL43032 A IL 43032A
- Authority
- IL
- Israel
- Prior art keywords
- accordance
- glyoxylic acid
- temperature
- aqueous solution
- dimethyl sulfate
- Prior art date
Links
- SSPYSWLZOPCOLO-UHFFFAOYSA-N 6-azauracil Chemical compound O=C1C=NNC(=O)N1 SSPYSWLZOPCOLO-UHFFFAOYSA-N 0.000 title claims 4
- 238000004519 manufacturing process Methods 0.000 title claims 4
- HHLFWLYXYJOTON-UHFFFAOYSA-N glyoxylic acid Chemical compound OC(=O)C=O HHLFWLYXYJOTON-UHFFFAOYSA-N 0.000 claims 16
- 238000000034 method Methods 0.000 claims 13
- 239000007864 aqueous solution Substances 0.000 claims 8
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 claims 7
- 238000006243 chemical reaction Methods 0.000 claims 5
- 239000000243 solution Substances 0.000 claims 5
- BRWIZMBXBAOCCF-UHFFFAOYSA-N hydrazinecarbothioamide Chemical compound NNC(N)=S BRWIZMBXBAOCCF-UHFFFAOYSA-N 0.000 claims 4
- 239000000203 mixture Substances 0.000 claims 4
- 238000010992 reflux Methods 0.000 claims 4
- LBPGMKDNBOKEEF-UHFFFAOYSA-N 2-(carbamothioylhydrazinylidene)acetic acid Chemical compound NC(=S)NN=CC(O)=O LBPGMKDNBOKEEF-UHFFFAOYSA-N 0.000 claims 3
- 238000007363 ring formation reaction Methods 0.000 claims 3
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 claims 1
- 238000010924 continuous production Methods 0.000 claims 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 239000011541 reaction mixture Substances 0.000 claims 1
Landscapes
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Claims (15)
1. A process for the production of 6-azauracll. which comprises the steps of bringing together thiosemicarbazide, glyoxylic acid, and. dimethyl sulfate in. aqueous solution so as to permit the formation of β-azauracil; and recovering the product thus formed from the reaction mixture'.
2. The process in accordance With Claim 1 wherein said dimethyl sulfate is added to said aqueous solution after said thiosemicarbazlde and said glyoxylic acid have first been added thereto.
3. The process in accordance with Claim 2 wherein, for each mol of glyoxylic acid, there are used from about 1. 05 to about 1. 25 mols of thiosemicarbazlde; and from about 1. 1 to about h mols of dimethyl sulfate.
4. The process in accordance with Claim 2 wherein said thiosemicarbazlde and said glyoxylic acid are each separately made into aqueous solutions, and said glyoxylic acid solution is added to said thiosemicarbazlde solution.
5. ·. The process in accordance with Claim 2 wherein ■ said cyclization subsequent to the addition of said dimethyl' sulfate, is carried out at a temperature of at least 70°C.
6. The process in accordance with Claim 5 wherein said temperature is attained by refluxing.
7. A process for the production of 6-azauracil which comprises the steps of adding dimethyl sulfate to an aqueous solution of glyoxylic acid thiosemicarbazone; maintaining the mixture so formed at a temperature of at least 70°C. until cyclization of said glyoxylic acid thiosemicarbazone to said - u an n i roduct
8. The process in accordance with Claim 7 wherein from about 1.1 to about 4 mols of dimethyl sulfate are used for each mol of glyoxylic acid thiosemicarbazone .
9. The process in accordance with Claim 7 wherein said temperature is attained by refluxing.
10. The process in accordance with Claim 1 wherein said thiosemicarbazide and said dimethyl sulfate are first brought -together in aqueous solution, and said glyoxylic acid is subsequently- added to said aqueous solution. .
11. ,. ..The;,:ipr,o.c,e..ss ,,in ..ac o danee , it. —C-la,im -10•..wherein for each mol of thiosemicarbazide there are used from about 1.0 to about 1.8 mols of dimethyl sulfate; and from about 0.8 to about 1.5 mols of glyoxylic acid.
12. The process in accordance with Claim 10 wherein said cyclization is carried out at a temperature of at least 70°C.
13. A process in accordance with Claim 12 wherein said temperature is attained by refluxing.
14. A continuous process for the production of 6- azauracil in accordance with Claim.10 wherein said aqueous solution of thiosemicarbazide and said glyoxylic acid in aqueous solution form are each metered into a first vessel so as to become mixed together and heated to a preselected reaction temperature and wherein said solution mixture is continuously passed through a series of reaction vessels maintained at said preselected reaction temperature, and wherein said solution mixture exiting from the last of said reaction vessels is cooled and said 6-azauracil is collected therefrom.
15. The process in accordance with Claim 14 wherein said preselected reaction temperature is the temperature at which said solution mixture refluxes..
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IL43032A IL43032A (en) | 1973-08-20 | 1973-08-20 | The production of 6-azauracil |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IL43032A IL43032A (en) | 1973-08-20 | 1973-08-20 | The production of 6-azauracil |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL43032A0 IL43032A0 (en) | 1973-11-28 |
| IL43032A true IL43032A (en) | 1976-03-31 |
Family
ID=11047292
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL43032A IL43032A (en) | 1973-08-20 | 1973-08-20 | The production of 6-azauracil |
Country Status (1)
| Country | Link |
|---|---|
| IL (1) | IL43032A (en) |
-
1973
- 1973-08-20 IL IL43032A patent/IL43032A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| IL43032A0 (en) | 1973-11-28 |
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