JPS60258177A - テトラヒドロピラン−２−オキシエチルジチオカルバミン酸ベンジルエステルの製造法 - Google Patents
テトラヒドロピラン−２−オキシエチルジチオカルバミン酸ベンジルエステルの製造法Info
- Publication number
- JPS60258177A JPS60258177A JP11477984A JP11477984A JPS60258177A JP S60258177 A JPS60258177 A JP S60258177A JP 11477984 A JP11477984 A JP 11477984A JP 11477984 A JP11477984 A JP 11477984A JP S60258177 A JPS60258177 A JP S60258177A
- Authority
- JP
- Japan
- Prior art keywords
- benzyl
- ethanolamine
- dithiocarbamate
- tetrahydropyran
- formula
- 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.)
- Granted
Links
- JOSWPMLQRIAKNN-UHFFFAOYSA-N benzyl n-[2-(oxan-2-yloxy)ethyl]carbamodithioate Chemical compound C=1C=CC=CC=1CSC(=S)NCCOC1CCCCO1 JOSWPMLQRIAKNN-UHFFFAOYSA-N 0.000 title claims description 7
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 claims abstract description 24
- -1 Benzyl tetrahydropyran-2-oxyethyl-dithiocarbamate Chemical compound 0.000 claims abstract description 16
- 150000003512 tertiary amines Chemical class 0.000 claims abstract description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 9
- PDGZYJPVVVQCIY-UHFFFAOYSA-N benzyl n-(2-hydroxyethyl)carbamodithioate Chemical compound OCCNC(=S)SCC1=CC=CC=C1 PDGZYJPVVVQCIY-UHFFFAOYSA-N 0.000 claims abstract description 6
- 229910052783 alkali metal Inorganic materials 0.000 claims abstract description 5
- 150000001340 alkali metals Chemical class 0.000 claims abstract description 5
- VKLXPBBZKVZDLB-UHFFFAOYSA-N 2-hydroxyethyl carbamodithioate Chemical compound NC(=S)SCCO VKLXPBBZKVZDLB-UHFFFAOYSA-N 0.000 claims abstract 3
- 238000006243 chemical reaction Methods 0.000 claims description 16
- 239000002904 solvent Substances 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 4
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 claims description 4
- 229940073608 benzyl chloride Drugs 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- QGJOPFRUJISHPQ-NJFSPNSNSA-N carbon disulfide-14c Chemical compound S=[14C]=S QGJOPFRUJISHPQ-NJFSPNSNSA-N 0.000 claims 2
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 3
- 239000002994 raw material Substances 0.000 abstract description 3
- XOTPCOBRQLBTAD-UHFFFAOYSA-N 1-(1-hydroxyethyl)-2h-tetrazole-5-thione Chemical compound CC(O)N1N=NN=C1S XOTPCOBRQLBTAD-UHFFFAOYSA-N 0.000 abstract description 2
- 239000012442 inert solvent Substances 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 19
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 230000032683 aging Effects 0.000 description 8
- 239000013078 crystal Substances 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 239000012990 dithiocarbamate Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 238000000862 absorption spectrum Methods 0.000 description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 239000012433 hydrogen halide Substances 0.000 description 2
- 229910000039 hydrogen halide Inorganic materials 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 230000005070 ripening Effects 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- MMLBEXXDOLIGCR-UHFFFAOYSA-N 2-hydroxyethylcarbamodithioic acid Chemical compound OCCNC(S)=S MMLBEXXDOLIGCR-UHFFFAOYSA-N 0.000 description 1
- MGADZUXDNSDTHW-UHFFFAOYSA-N 2H-pyran Chemical compound C1OC=CC=C1 MGADZUXDNSDTHW-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- DKVNPHBNOWQYFE-UHFFFAOYSA-N carbamodithioic acid Chemical compound NC(S)=S DKVNPHBNOWQYFE-UHFFFAOYSA-N 0.000 description 1
- DXHPZXWIPWDXHJ-UHFFFAOYSA-N carbon monosulfide Chemical compound [S+]#[C-] DXHPZXWIPWDXHJ-UHFFFAOYSA-N 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 239000012454 non-polar solvent Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 239000013077 target material Substances 0.000 description 1
Landscapes
- Pyrane Compounds (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP11477984A JPS60258177A (ja) | 1984-06-04 | 1984-06-04 | テトラヒドロピラン−２−オキシエチルジチオカルバミン酸ベンジルエステルの製造法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP11477984A JPS60258177A (ja) | 1984-06-04 | 1984-06-04 | テトラヒドロピラン−２−オキシエチルジチオカルバミン酸ベンジルエステルの製造法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS60258177A true JPS60258177A (ja) | 1985-12-20 |
| JPH0544465B2 JPH0544465B2 (enrdf_load_stackoverflow) | 1993-07-06 |
Family
ID=14646468
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP11477984A Granted JPS60258177A (ja) | 1984-06-04 | 1984-06-04 | テトラヒドロピラン−２−オキシエチルジチオカルバミン酸ベンジルエステルの製造法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS60258177A (enrdf_load_stackoverflow) |
-
1984
- 1984-06-04 JP JP11477984A patent/JPS60258177A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0544465B2 (enrdf_load_stackoverflow) | 1993-07-06 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| SE462096B (sv) | Dicyklohexylammonium-6 beta-brompenicillanat vilken aer anvaendbar saasom mellanprodukt | |
| JP2941287B2 (ja) | ２，４，６−トリメルカプト−ｓ−トリアジン−９−水和物の３ナトリウム塩の製造法 | |
| JP2004511475A (ja) | ラセミ体チオクト酸の製造方法 | |
| EP0950664A1 (en) | Process for producing n-glycyltyrosine | |
| JPS60258177A (ja) | テトラヒドロピラン−２−オキシエチルジチオカルバミン酸ベンジルエステルの製造法 | |
| JP4689803B2 (ja) | （２ｓ，４ｓ）−ｎ，ｎ−ジメチル−１−アリルオキシカルボニル−４−ベンゾイルチオ−２−ピロリジンカルボキサミドの製造方法 | |
| US5300274A (en) | Method for making molybdenum and sulfur containing compounds | |
| SU1215622A3 (ru) | Способ получени производных сульфимида @ -карбамоилбензойной кислоты | |
| EP0111569B1 (en) | Hydroxyalkanesulfonic acids and their derivatives, and process for their preparation | |
| KR860001900B1 (ko) | β-클로로 아라닌의 제조법 | |
| JPS61218555A (ja) | トリフルオロジクロロエチル基により置換された酸類の製法および亜鉛化合物類 | |
| JP3032386B2 (ja) | Ｎ−グアニジノチオ尿素塩及び３−アミノ−５−メルカプト−１，２，４−トリアゾールの製造方法 | |
| US4515958A (en) | Process for preparing 1-alkyl-5-mercaptotetrazoles | |
| US5071982A (en) | Process for producing a 4,6-bis(difluoromethoxy)-2-alkylthiopyrimidine | |
| JPS60258143A (ja) | ２，３，５，６−テトラフルオロ安息香酸の製造方法 | |
| EP0435073A1 (de) | Sulfonierte Propylphenylphosphane, ihre Herstellung und Verwendung | |
| SU1724580A1 (ru) | Способ получени тетратиоарсената натри | |
| WO1995029126A1 (en) | A method for making molybdenum and sulfur containing compounds | |
| WO1995021828A1 (fr) | Procede de production de derives de l'hexahydropyridazine et de l'hexahydropyridazine-1,2-dicarboxylate | |
| JPS6152145B2 (enrdf_load_stackoverflow) | ||
| JPS63179854A (ja) | 硫化ビス（エトキシチオカルボニル）の合成法 | |
| SU627129A1 (ru) | 4-Хлор-5,7-динитробензофуразан в качестве промежуточного продукта в синтезе 4-замещенных-5,7-динитробензофуразанов | |
| JPS6155914B2 (enrdf_load_stackoverflow) | ||
| JPS58157797A (ja) | ３，５，６−トリ−Ｏ−ベンジル−１，２−Ｏ−イソプロピリデン−α−Ｄ−グルコフラノ−スの製造法 | |
| JPH02215752A (ja) | アセキサミン酸誘導体の製造方法 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EXPY | Cancellation because of completion of term |