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 (enExample) | 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 (enExample) |
-
1984
- 1984-06-04 JP JP11477984A patent/JPS60258177A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0544465B2 (enExample) | 1993-07-06 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EXPY | Cancellation because of completion of term |