CN110343059A - 制备烷氧羰基异硫氰酸酯的方法 - Google Patents
制备烷氧羰基异硫氰酸酯的方法 Download PDFInfo
- Publication number
- CN110343059A CN110343059A CN201910678192.4A CN201910678192A CN110343059A CN 110343059 A CN110343059 A CN 110343059A CN 201910678192 A CN201910678192 A CN 201910678192A CN 110343059 A CN110343059 A CN 110343059A
- Authority
- CN
- China
- Prior art keywords
- catalyst
- alkyl
- pyridine
- molar equivalent
- rhodanate
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims abstract description 41
- -1 alkoxycarbonyl isothiocyanate Chemical class 0.000 title claims abstract description 26
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims abstract description 27
- 239000003054 catalyst Substances 0.000 claims abstract description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 17
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 28
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical group C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 18
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical group N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 18
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 claims description 18
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Chemical group COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 14
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Chemical group C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims description 9
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical group C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
- 159000000000 sodium salts Chemical group 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 150000002367 halogens Chemical group 0.000 claims description 5
- 235000011164 potassium chloride Nutrition 0.000 claims description 5
- 239000001103 potassium chloride Substances 0.000 claims description 5
- 150000003863 ammonium salts Chemical class 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- 150000002391 heterocyclic compounds Chemical class 0.000 claims 1
- 239000000243 solution Substances 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 5
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 4
- VGTPCRGMBIAPIM-UHFFFAOYSA-M sodium thiocyanate Chemical compound [Na+].[S-]C#N VGTPCRGMBIAPIM-UHFFFAOYSA-M 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 3
- BDTDECDAHYOJRO-UHFFFAOYSA-N ethyl n-(sulfanylidenemethylidene)carbamate Chemical compound CCOC(=O)N=C=S BDTDECDAHYOJRO-UHFFFAOYSA-N 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 description 2
- 238000010813 internal standard method Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000005864 Sulphur Substances 0.000 description 1
- PWSLFNJJGHXGMS-UHFFFAOYSA-N [Cl].CCOC=O Chemical compound [Cl].CCOC=O PWSLFNJJGHXGMS-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- SOIFLUNRINLCBN-UHFFFAOYSA-N ammonium thiocyanate Chemical compound [NH4+].[S-]C#N SOIFLUNRINLCBN-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 150000003851 azoles Chemical class 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000003426 co-catalyst Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000006184 cosolvent Substances 0.000 description 1
- XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000009795 derivation Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- JMANVNJQNLATNU-UHFFFAOYSA-N glycolonitrile Natural products N#CC#N JMANVNJQNLATNU-UHFFFAOYSA-N 0.000 description 1
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 1
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- LJXQPZWIHJMPQQ-UHFFFAOYSA-N pyrimidin-2-amine Chemical compound NC1=NC=CC=N1 LJXQPZWIHJMPQQ-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003567 thiocyanates Chemical class 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 238000003809 water extraction Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C331/00—Derivatives of thiocyanic acid or of isothiocyanic acid
- C07C331/16—Isothiocyanates
- C07C331/32—Isothiocyanates having isothiocyanate groups acylated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Pyridine Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201261711868P | 2012-10-10 | 2012-10-10 | |
| US61/711,868 | 2012-10-10 | ||
| CN201380052441.XA CN104736517A (zh) | 2012-10-10 | 2013-10-09 | 制备烷氧羰基异硫氰酸酯的方法 |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201380052441.XA Division CN104736517A (zh) | 2012-10-10 | 2013-10-09 | 制备烷氧羰基异硫氰酸酯的方法 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN110343059A true CN110343059A (zh) | 2019-10-18 |
Family
ID=50433197
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201910678192.4A Pending CN110343059A (zh) | 2012-10-10 | 2013-10-09 | 制备烷氧羰基异硫氰酸酯的方法 |
| CN201380052441.XA Pending CN104736517A (zh) | 2012-10-10 | 2013-10-09 | 制备烷氧羰基异硫氰酸酯的方法 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201380052441.XA Pending CN104736517A (zh) | 2012-10-10 | 2013-10-09 | 制备烷氧羰基异硫氰酸酯的方法 |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US8933260B2 (enExample) |
| EP (1) | EP2906533B1 (enExample) |
| JP (1) | JP6267209B2 (enExample) |
| KR (1) | KR102137456B1 (enExample) |
| CN (2) | CN110343059A (enExample) |
| AU (1) | AU2013329365B2 (enExample) |
| BR (1) | BR102013026072A2 (enExample) |
| CA (1) | CA2887482A1 (enExample) |
| HK (1) | HK1213240A1 (enExample) |
| IL (2) | IL238151A (enExample) |
| IN (1) | IN2015DN03009A (enExample) |
| MX (1) | MX2015004561A (enExample) |
| PL (1) | PL2906533T3 (enExample) |
| RU (1) | RU2015117526A (enExample) |
| WO (1) | WO2014058996A1 (enExample) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105481740B (zh) * | 2015-12-24 | 2017-11-07 | 海利贵溪化工农药有限公司 | 异硫氰基甲酸甲酯的制备方法 |
| CN109675723B (zh) * | 2019-01-29 | 2021-07-06 | 中南大学 | 具有酰胺基和硫代酰胺基的捕收剂及其制备方法和应用 |
| CN110343058A (zh) * | 2019-07-22 | 2019-10-18 | 湖南速博生物技术有限公司 | 一种异硫氰基化合物的制备方法 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4659853A (en) * | 1986-01-22 | 1987-04-21 | American Cyanamid Company | Process for the production of isothiocyanate derivatives |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4778921A (en) | 1986-01-22 | 1988-10-18 | American Cyanamid Company | Novel process of alkoxy and aryloxy isothiocyanate preparation |
| US5194673A (en) * | 1992-07-27 | 1993-03-16 | American Cyanamid Company | Process of alkoxy and aryloxy isothiocyanate preparation |
| US8143395B2 (en) | 2010-05-25 | 2012-03-27 | Dow Agrosciences Llc | Process for the preparation of 5-substituted-8-alkoxy[1,2,4]triazolo[1,5-c]pyrimidin-2-amines |
-
2013
- 2013-10-09 KR KR1020157011790A patent/KR102137456B1/ko active Active
- 2013-10-09 AU AU2013329365A patent/AU2013329365B2/en not_active Ceased
- 2013-10-09 IN IN3009DEN2015 patent/IN2015DN03009A/en unknown
- 2013-10-09 CN CN201910678192.4A patent/CN110343059A/zh active Pending
- 2013-10-09 CN CN201380052441.XA patent/CN104736517A/zh active Pending
- 2013-10-09 BR BR102013026072-0A patent/BR102013026072A2/pt not_active Application Discontinuation
- 2013-10-09 JP JP2015536858A patent/JP6267209B2/ja active Active
- 2013-10-09 HK HK16101192.6A patent/HK1213240A1/zh unknown
- 2013-10-09 WO PCT/US2013/064090 patent/WO2014058996A1/en not_active Ceased
- 2013-10-09 RU RU2015117526A patent/RU2015117526A/ru unknown
- 2013-10-09 US US14/049,820 patent/US8933260B2/en active Active
- 2013-10-09 PL PL13845734T patent/PL2906533T3/pl unknown
- 2013-10-09 EP EP13845734.6A patent/EP2906533B1/en active Active
- 2013-10-09 MX MX2015004561A patent/MX2015004561A/es unknown
- 2013-10-09 CA CA2887482A patent/CA2887482A1/en not_active Abandoned
-
2015
- 2015-04-02 IL IL238151A patent/IL238151A/en active IP Right Grant
- 2015-04-12 IL IL238201A patent/IL238201A0/en unknown
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4659853A (en) * | 1986-01-22 | 1987-04-21 | American Cyanamid Company | Process for the production of isothiocyanate derivatives |
Also Published As
| Publication number | Publication date |
|---|---|
| EP2906533A4 (en) | 2016-05-18 |
| JP2015534583A (ja) | 2015-12-03 |
| KR102137456B1 (ko) | 2020-07-24 |
| US8933260B2 (en) | 2015-01-13 |
| AU2013329365B2 (en) | 2016-03-17 |
| CN104736517A (zh) | 2015-06-24 |
| IL238201A0 (en) | 2015-05-31 |
| KR20150064749A (ko) | 2015-06-11 |
| EP2906533A1 (en) | 2015-08-19 |
| RU2015117526A (ru) | 2016-11-27 |
| HK1213240A1 (zh) | 2016-06-30 |
| MX2015004561A (es) | 2015-07-14 |
| WO2014058996A1 (en) | 2014-04-17 |
| CA2887482A1 (en) | 2014-04-17 |
| IN2015DN03009A (enExample) | 2015-10-02 |
| US20140100381A1 (en) | 2014-04-10 |
| JP6267209B2 (ja) | 2018-01-24 |
| PL2906533T3 (pl) | 2019-08-30 |
| EP2906533B1 (en) | 2019-02-27 |
| AU2013329365A1 (en) | 2015-04-30 |
| BR102013026072A2 (pt) | 2014-11-04 |
| IL238151A (en) | 2017-05-29 |
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| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| WD01 | Invention patent application deemed withdrawn after publication |
Application publication date: 20191018 |
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| WD01 | Invention patent application deemed withdrawn after publication |