BE503014A - - Google Patents
Info
- Publication number
- BE503014A BE503014A BE503014DA BE503014A BE 503014 A BE503014 A BE 503014A BE 503014D A BE503014D A BE 503014DA BE 503014 A BE503014 A BE 503014A
- Authority
- BE
- Belgium
- Prior art keywords
- phthalaldehyde
- thiosemicarbazide
- solution
- mol
- production
- Prior art date
Links
- BRWIZMBXBAOCCF-UHFFFAOYSA-N aminothiourea Chemical compound NNC(N)=S BRWIZMBXBAOCCF-UHFFFAOYSA-N 0.000 claims description 10
- ZWLUXSQADUDCSB-UHFFFAOYSA-N Phthalaldehyde Chemical class O=CC1=CC=CC=C1C=O ZWLUXSQADUDCSB-UHFFFAOYSA-N 0.000 claims description 9
- 238000006243 chemical reaction Methods 0.000 claims description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 9
- 239000002904 solvent Substances 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- 229940042396 direct acting antivirals Thiosemicarbazones Drugs 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 3
- 238000001953 recrystallisation Methods 0.000 claims description 3
- 150000003584 thiosemicarbazones Chemical class 0.000 claims description 3
- 238000003756 stirring Methods 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims 1
- 125000003172 aldehyde group Chemical group 0.000 claims 1
- 238000009835 boiling Methods 0.000 claims 1
- 238000009827 uniform distribution Methods 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- KUCOHFSKRZZVRO-UHFFFAOYSA-N terephthalaldehyde Chemical compound O=CC1=CC=C(C=O)C=C1 KUCOHFSKRZZVRO-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 4
- 235000011121 sodium hydroxide Nutrition 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- WUBBRNOQWQTFEX-UHFFFAOYSA-N 4-Aminosalicylic acid Chemical compound NC1=CC=C(C(O)=O)C(O)=C1 WUBBRNOQWQTFEX-UHFFFAOYSA-N 0.000 description 2
- 229960000583 Acetic Acid Drugs 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- 238000007792 addition Methods 0.000 description 2
- 229960004909 aminosalicylic acid Drugs 0.000 description 2
- IZALUMVGBVKPJD-UHFFFAOYSA-N benzene-1,3-dicarbaldehyde Chemical compound O=CC1=CC=CC(C=O)=C1 IZALUMVGBVKPJD-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 230000000875 corresponding Effects 0.000 description 2
- 238000005755 formation reaction Methods 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N n-butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 230000002035 prolonged Effects 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 1
- 241001474791 Proboscis Species 0.000 description 1
- ATTFZKKNUFOHRF-UHFFFAOYSA-N [(4-formylphenyl)methylideneamino]thiourea Chemical compound NC(=S)NN=CC1=CC=C(C=O)C=C1 ATTFZKKNUFOHRF-UHFFFAOYSA-N 0.000 description 1
- VTZWNSAFVYMODF-ACFHMISVSA-N [(E)-[4-[(E)-(carbamothioylhydrazinylidene)methyl]phenyl]methylideneamino]thiourea Chemical compound NC(=S)N\N=C\C1=CC=C(\C=N\NC(N)=S)C=C1 VTZWNSAFVYMODF-ACFHMISVSA-N 0.000 description 1
- SYDDDECKVFWDCK-UHFFFAOYSA-N [[2-[(carbamothioylhydrazinylidene)methyl]phenyl]methylideneamino]thiourea Chemical compound NC(=S)NN=CC1=CC=CC=C1C=NNC(N)=S SYDDDECKVFWDCK-UHFFFAOYSA-N 0.000 description 1
- BPBGBZSSUXXWPS-UHFFFAOYSA-N [[3-[(carbamothioylhydrazinylidene)methyl]phenyl]methylideneamino]thiourea Chemical compound NC(=S)NN=CC1=CC=CC(C=NNC(N)=S)=C1 BPBGBZSSUXXWPS-UHFFFAOYSA-N 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 229940054441 o-Phthalaldehyde Drugs 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- GRYBZNLNHVSHPY-UHFFFAOYSA-N sodium;4-hydroxy-5-[(6-oxocyclohexa-2,4-dien-1-ylidene)methylamino]naphthalene-2,7-disulfonic acid Chemical class [Na+].C=12C(O)=CC(S(O)(=O)=O)=CC2=CC(S(O)(=O)=O)=CC=1NC=C1C=CC=CC1=O GRYBZNLNHVSHPY-UHFFFAOYSA-N 0.000 description 1
- 230000003381 solubilizing Effects 0.000 description 1
- 230000001225 therapeutic Effects 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BE503014A true BE503014A (de) |
Family
ID=144353
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BE503014D BE503014A (de) |
Country Status (1)
| Country | Link |
|---|---|
| BE (1) | BE503014A (de) |
-
0
- BE BE503014D patent/BE503014A/fr unknown
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