JPS622599B2 - - Google Patents
Info
- Publication number
- JPS622599B2 JPS622599B2 JP13768280A JP13768280A JPS622599B2 JP S622599 B2 JPS622599 B2 JP S622599B2 JP 13768280 A JP13768280 A JP 13768280A JP 13768280 A JP13768280 A JP 13768280A JP S622599 B2 JPS622599 B2 JP S622599B2
- Authority
- JP
- Japan
- Prior art keywords
- adenine
- phenyladenine
- formamide
- water
- crystals
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- GFFGJBXGBJISGV-UHFFFAOYSA-N Adenine Chemical compound NC1=NC=NC2=C1N=CN2 GFFGJBXGBJISGV-UHFFFAOYSA-N 0.000 claims description 76
- 229930024421 Adenine Natural products 0.000 claims description 75
- 229960000643 adenine Drugs 0.000 claims description 75
- QOZYZBRNUYGQNF-UHFFFAOYSA-N 9-phenylpurin-6-amine Chemical compound C1=NC=2C(N)=NC=NC=2N1C1=CC=CC=C1 QOZYZBRNUYGQNF-UHFFFAOYSA-N 0.000 claims description 41
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 29
- 238000000034 method Methods 0.000 claims description 26
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 53
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 30
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 28
- 239000013078 crystal Substances 0.000 description 27
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 18
- 239000007788 liquid Substances 0.000 description 18
- 238000006243 chemical reaction Methods 0.000 description 14
- 238000010438 heat treatment Methods 0.000 description 12
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 11
- 239000000203 mixture Substances 0.000 description 10
- 238000010992 reflux Methods 0.000 description 10
- 235000011121 sodium hydroxide Nutrition 0.000 description 10
- 239000000047 product Substances 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- 238000004519 manufacturing process Methods 0.000 description 8
- 230000002378 acidificating effect Effects 0.000 description 7
- 238000001914 filtration Methods 0.000 description 7
- DYDNPESBYVVLBO-UHFFFAOYSA-N formanilide Chemical compound O=CNC1=CC=CC=C1 DYDNPESBYVVLBO-UHFFFAOYSA-N 0.000 description 7
- KLMBASWITNCMTF-UHFFFAOYSA-N 2-phenyldiazenylpropanedinitrile Chemical compound N#CC(C#N)N=NC1=CC=CC=C1 KLMBASWITNCMTF-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 238000001953 recrystallisation Methods 0.000 description 6
- 150000003839 salts Chemical group 0.000 description 6
- 229910021529 ammonia Inorganic materials 0.000 description 5
- 238000000746 purification Methods 0.000 description 5
- YKMJOAVCSAOXOU-UHFFFAOYSA-N 2-phenyl-7h-purin-6-amine Chemical compound N=1C=2N=CNC=2C(N)=NC=1C1=CC=CC=C1 YKMJOAVCSAOXOU-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 3
- 229910000564 Raney nickel Inorganic materials 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 150000003948 formamides Chemical class 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- 235000011114 ammonium hydroxide Nutrition 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 239000007810 chemical reaction solvent Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- -1 methyl formate Chemical compound 0.000 description 2
- TZIHFWKZFHZASV-UHFFFAOYSA-N methyl formate Chemical compound COC=O TZIHFWKZFHZASV-UHFFFAOYSA-N 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 238000006722 reduction reaction Methods 0.000 description 2
- 238000001577 simple distillation Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- PNKUSGQVOMIXLU-UHFFFAOYSA-N Formamidine Chemical class NC=N PNKUSGQVOMIXLU-UHFFFAOYSA-N 0.000 description 1
- BDAGIHXWWSANSR-UHFFFAOYSA-N Formic acid Chemical class OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 1
- RLAHWVDQYNDAGG-UHFFFAOYSA-N Methanetriol Chemical class OC(O)O RLAHWVDQYNDAGG-UHFFFAOYSA-N 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- XPOLVIIHTDKJRY-UHFFFAOYSA-N acetic acid;methanimidamide Chemical compound NC=N.CC(O)=O XPOLVIIHTDKJRY-UHFFFAOYSA-N 0.000 description 1
- 239000003463 adsorbent Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- LYFFZYAHRGUALV-UHFFFAOYSA-N azane formamide Chemical class N.NC=O LYFFZYAHRGUALV-UHFFFAOYSA-N 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 238000010531 catalytic reduction reaction Methods 0.000 description 1
- 239000003729 cation exchange resin Substances 0.000 description 1
- 229920001429 chelating resin Polymers 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 150000004292 cyclic ethers Chemical class 0.000 description 1
- 238000004042 decolorization Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
- 150000004675 formic acid derivatives Chemical class 0.000 description 1
- WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000006193 liquid solution Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000010446 mirabilite Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 238000006864 oxidative decomposition reaction Methods 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000012286 potassium permanganate Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- RSIJVJUOQBWMIM-UHFFFAOYSA-L sodium sulfate decahydrate Chemical compound O.O.O.O.O.O.O.O.O.O.[Na+].[Na+].[O-]S([O-])(=O)=O RSIJVJUOQBWMIM-UHFFFAOYSA-L 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP13768280A JPS5762279A (en) | 1980-10-03 | 1980-10-03 | Purifying method of adenine |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP13768280A JPS5762279A (en) | 1980-10-03 | 1980-10-03 | Purifying method of adenine |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5762279A JPS5762279A (en) | 1982-04-15 |
| JPS622599B2 true JPS622599B2 (cs) | 1987-01-20 |
Family
ID=15204343
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP13768280A Granted JPS5762279A (en) | 1980-10-03 | 1980-10-03 | Purifying method of adenine |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5762279A (cs) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS602578A (ja) * | 1983-06-17 | 1985-01-08 | 三菱電機株式会社 | エレベ−タの管理装置 |
-
1980
- 1980-10-03 JP JP13768280A patent/JPS5762279A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5762279A (en) | 1982-04-15 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN109836424B (zh) | 一种环保型茶碱钠盐甲基化制备咖啡因的方法 | |
| JPS622599B2 (cs) | ||
| US5767318A (en) | Process for producing a high purity 2,4-dihydroxydiphenylsulfone | |
| JP3182946B2 (ja) | Ｎ−（α−アルコキシエチル）ホルムアミドの製造方法 | |
| US3397231A (en) | Refining of alpha-6-deoxy-5-oxytetracycline | |
| JPS5855485A (ja) | グアニンの精製法 | |
| US2475673A (en) | Aminobenzenesulfonamidohalopyrazines and method of preparing same | |
| JP6275596B2 (ja) | テルミサルタンのアンモニウム塩の製造方法 | |
| JPH04360879A (ja) | 芳香族トリアゾール類の精製方法 | |
| JP3407336B2 (ja) | アミノエタンスルホン酸類の精製方法 | |
| JPH0796537B2 (ja) | ３−（３，４−ジヒドロキシフェニル）セリンの精製方法 | |
| JP2008222593A (ja) | アルキルアミノピリジン類の精製方法 | |
| JP2626710B2 (ja) | ４−アミノ−１，２，４−（４ｈ）トリアゾール誘導体の合成方法 | |
| KR850000717B1 (ko) | 단백질 가수분해 산물로 부터의 아미노산의 회수방법 | |
| JPS6337104B2 (cs) | ||
| JPS6327477A (ja) | オキシラセタムの製造方法 | |
| JP2003096039A (ja) | 高純度ｎ−長鎖アシルアミノ酸塩の製造法 | |
| JPH01190661A (ja) | ４，４′−ジヒドロキシジフエニルスルホンの精製法 | |
| JP2770512B2 (ja) | アミノエチルスルホン酸アルカリ金属塩類の精製方法 | |
| JP2004182668A (ja) | ジヒドロキシジフェニルスルホン異性体混合物の製造方法 | |
| RU2022103872A (ru) | Способ получения ридинилазола и его кристаллических форм | |
| JPS6157537A (ja) | クロロアラニンの精製法 | |
| CN117088939A (zh) | 一种匹多莫德的制备方法 | |
| JPS623839B2 (cs) | ||
| JPS6337105B2 (cs) |