CN1696126A - 二氟苯并－1,3－间二氧杂环戊烯 - Google Patents
二氟苯并－1,3－间二氧杂环戊烯 Download PDFInfo
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- 238000000034 method Methods 0.000 title claims abstract description 9
- 238000002360 preparation method Methods 0.000 title claims abstract description 9
- SZRHWHHXVXSGMT-UHFFFAOYSA-N 5-bromo-2,2-difluoro-1,3-benzodioxole Chemical class C1=C(Br)C=C2OC(F)(F)OC2=C1 SZRHWHHXVXSGMT-UHFFFAOYSA-N 0.000 title 1
- 239000003814 drug Substances 0.000 claims abstract description 5
- 150000001875 compounds Chemical class 0.000 claims description 16
- -1 cyano, nitro, iodo Chemical group 0.000 claims description 15
- 125000001153 fluoro group Chemical group F* 0.000 claims description 5
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
- PKCOTODGEAJGQZ-UHFFFAOYSA-N 2,2-difluoro-5-isothiocyanato-1,3-benzodioxole Chemical compound C1=C(N=C=S)C=C2OC(F)(F)OC2=C1 PKCOTODGEAJGQZ-UHFFFAOYSA-N 0.000 claims description 3
- 239000003905 agrochemical Substances 0.000 claims description 3
- 125000001246 bromo group Chemical group Br* 0.000 claims description 3
- 239000000543 intermediate Substances 0.000 claims description 2
- 150000002540 isothiocyanates Chemical class 0.000 claims description 2
- RBLZMQODVSLEHV-UHFFFAOYSA-N 1-sulfanylimidazolidin-2-one Chemical compound SN1CCNC1=O RBLZMQODVSLEHV-UHFFFAOYSA-N 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- BOIUBJYPHIFHEJ-UHFFFAOYSA-N 2,4-difluoro-1,3-benzodioxole Chemical class C1=CC(F)=C2OC(F)OC2=C1 BOIUBJYPHIFHEJ-UHFFFAOYSA-N 0.000 abstract description 7
- 239000011814 protection agent Substances 0.000 abstract description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 125000003545 alkoxy group Chemical group 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 238000006467 substitution reaction Methods 0.000 description 3
- CVYQRDKVWVBOFP-UHFFFAOYSA-N 2,2-difluoro-1,3-benzodioxol-5-amine Chemical compound NC1=CC=C2OC(F)(F)OC2=C1 CVYQRDKVWVBOFP-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 150000002527 isonitriles Chemical class 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
- ZWZVWGITAAIFPS-UHFFFAOYSA-N thiophosgene Chemical compound ClC(Cl)=S ZWZVWGITAAIFPS-UHFFFAOYSA-N 0.000 description 2
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 description 1
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 description 1
- FKTXDTWDCPTPHK-UHFFFAOYSA-N 1,1,1,2,3,3,3-heptafluoropropane Chemical group FC(F)(F)[C](F)C(F)(F)F FKTXDTWDCPTPHK-UHFFFAOYSA-N 0.000 description 1
- FIARMZDBEGVMLV-UHFFFAOYSA-N 1,1,2,2,2-pentafluoroethanolate Chemical group [O-]C(F)(F)C(F)(F)F FIARMZDBEGVMLV-UHFFFAOYSA-N 0.000 description 1
- 125000006219 1-ethylpentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- IDBKKNKUXGXSFJ-UHFFFAOYSA-N 1h-imidazole-2-carbothioyl chloride Chemical compound ClC(=S)C1=NC=CN1 IDBKKNKUXGXSFJ-UHFFFAOYSA-N 0.000 description 1
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 1
- GOZOPWOQEBNBAJ-UHFFFAOYSA-N 5-bromo-2,4-difluoro-1,3-benzodioxole Chemical compound C1=C(Br)C(F)=C2OC(F)OC2=C1 GOZOPWOQEBNBAJ-UHFFFAOYSA-N 0.000 description 1
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- RAFNCPHFRHZCPS-UHFFFAOYSA-N di(imidazol-1-yl)methanethione Chemical compound C1=CN=CN1C(=S)N1C=CN=C1 RAFNCPHFRHZCPS-UHFFFAOYSA-N 0.000 description 1
- 125000004428 fluoroalkoxy group Chemical group 0.000 description 1
- 125000003709 fluoroalkyl group Chemical group 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000005246 nonafluorobutyl group Chemical group FC(F)(F)C(F)(F)C(F)(F)C(F)(F)* 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
- 125000005007 perfluorooctyl group Chemical group FC(C(C(C(C(C(C(C(F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)* 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 150000003254 radicals Chemical class 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
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000725 suspension Substances 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
- 150000003558 thiocarbamic acid derivatives Chemical class 0.000 description 1
- FAWIHCUUQFGNFK-UHFFFAOYSA-N thiocarbonyl dichloride Chemical compound ClC(Cl)=S.ClC(Cl)=S FAWIHCUUQFGNFK-UHFFFAOYSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
本发明涉及二氟苯并－1，3－间二氧杂环戊烯化合物，涉及所述化合物的制备方法，以及它们在制备药物和农作物保护剂方面的用途。
Description
技术领域
本发明涉及二氟苯并-1，3-间二氧杂环戊烯化合物，涉及这些化合物的制备方法，以及它们在制备药物和农作物保护剂方面的用途。
背景技术
二氟苯并-1，3-间二氧杂环戊烯化合物是农药以及药物活性组分的重要结构单元；还可参见WO 02/81453，尤其是实施例321。为了能够把二氟苯并-1，3-间二氧杂环戊烯结构单元引入活性组分分子中，5-溴二氟苯并-1，3-间二氧杂环戊烯要通过一个钯催化的转化过程，而这一过程从工业角度来看是很昂贵的。因此，有必要提供二氟苯并-1，3-间二氧杂环戊烯化合物，利用其内在的官能团就能以简单方法引入活性组分分子中，同时可用简单有效的方法制备该化合物。
发明内容
已经发现式(I)的化合物：
其中，
R1是C1-C12烷基、C1-C12氟代烷基、C1-C12烷氧基、C1-C12氟代烷氧基、氰基、硝基、碘、溴、氯或氟、以及
n是0、1、2或3。
式(I)化合物可以用WO 02/81453中述及的简单方式转化为本文所述的硫代咪唑啉酮(thioxoimidazolinones)。
同样已经发现了制备式(I)的化合物的方法，该方法的特征在于，原则上可用一种已知方式将以下的式(II)化合物转化为对应的异硫氰酸酯(或盐)。
式中，R1和n的定义如上所述。
优选的方法包括：
与硫代碳酰氯(thiophosgene)或其它硫代氨基甲酸衍生物(尤其是氯硫代羰基咪唑或者硫代羰基二咪唑)进行反应。
或者
在碱金属碱存在的条件下与二硫化碳反应，然后与氧化剂反应或者与碳酰氯或草酰氯反应。
或者
制备相应的异腈或异腈二卤化物(isocyanide dihalide)，然后进行硫化。
与硫代碳酰氯进行反应是优选的，而且该反应可有利地在水-酸性介质中进行。
所述的反应方法就其原理而言在文献中是熟知的。作为起始化合物的式(II)化合物既是文献中已知的，也可以参照与文献相类似的方法进行制备。已知二氟苯并间二氧杂环戊烯官能团是不稳定的、热敏感的、而且对于卤素置换是很敏感的，然而非常令人惊奇的是，所述反应基本上并未对该官能团造成影响。
本发明的范围包括所有的定义、参数和说明，无论是上文还是下文，无论是一般性范围内还是优选范围内，也可是上述的任意组合(也就是特定范围与优选范围之间的组合)。
烷基和烷氧基各自独立地是直链的、环状的、分支或未分支的烷基和烷氧基残基，所述的残基还可以任选地进一步被C1-C4-烷氧基替换。
例如，C1-C12-烷基可以是(而且优选地是)：甲基、乙基、正丙基、异丙基、正丁基、仲丁基、叔丁基、正戊基、1-甲基丁基、2-甲基丁基、3-甲基丁基、新戊基、1-乙基戊基、环己基、环戊基、正己基、正庚基、正辛基、正癸基和正十二烷基。
例如，C1-C12-烷氧基可以是(而且优选地是)：甲氧基、乙氧基、正丙氧基、异丙氧基、正丁氧基、仲丁氧基、叔丁氧基、正戊氧基、环己氧基、环戊氧基、正己氧基、正庚氧基、正辛氧基、正癸氧基和正十二烷氧基。
在每种情况下，氟代烷基和氟代烷氧基分别是被1个、多个氟原子替换或全部被氟原子替换的，直链的、环状的、分支或未分支的烷基残基和烷氧基残基。
例如，C1-C12-氟代烷基可以是三氟甲基、2，2，2-三氟乙基、五氟乙基、九氟丁基、七氟异丙基、全氟辛基和全氟十二烷基。
例如，C1-C12-氟烷氧基可以是三氟甲氧基、2，2，2-三氟乙氧基、五氟乙氧基、九氟丁氧基、七氟异丙氧基、全氟辛氧基和全氟十二烷氧基。
式(I)和(II)的化合物优选的取代形式如下所述：
R1较佳地是甲基、乙基、正丙基、氯、氟和溴，最佳地是氯或氟。
N较佳地是0，1或2，更佳地是0或1，最佳地是0。
一种特别优选的式(I)的化合物是5-异硫氰酸基-2，2-二氟苯并-1，3-间二氧杂环戊烯(5-isothiocyanato-2，2-difluorobenzo-1，3-dioxole)。
一种特别优选的式(II)的化合物是5-氨基-2，2-二氟苯并-1，3-间二氧杂环戊烯。
所发明的式(I)的化合物尤其适用于制备药物、农用化学品或其中间体。式(I)的化合物优先用于制备硫代咪唑啉酮，尤其是用于如WO 02/81453中所述的硫代咪唑啉酮。
具体实施方式
实施例1：
5-异硫氰酸基-2，2-二氟苯并[1，3]-间二氧杂环戊烯的制备：将34.6g 5-氨基-2，2-二氟苯并间二氧杂环戊烯滴加到90ml浓盐酸与350ml水的混合溶液中。该混合物再经过30分钟搅拌，然后迅速定量加入27g硫代碳酰氯。该混合物在给定温度下进一步搅拌3小时，将近乎无色的悬浮液与150ml二氯甲烷混合，然后除去二氯甲烷。在45毫巴(mbar)的条件下蒸馏该粗产物。得到28g(＝89％的理论产量)的无色至黄色的液体。
沸点：136℃/45 mbar
1H NMR(400MHz，CDCl6)：6.96(m，2H)，7.02(m，1H)
Claims (5)
1.式(I)的化合物，
其中，
R1是C1-C12烷基、C1-C12氟代烷基、C1-C12烷氧基、C1-C12氟代烷氧基、氰基、硝基、碘、溴、氯或氟；以及
n是0、1、2或3。
2.如权利要求1所述的化合物，其特征在于，它是5-异硫氰酸基-2，2-二氟苯并-1，3-间二氧杂环戊烯。
3.如权利要求1所述的化合物的制备方法，其特征在于，将式(II)的化合物转化为对应的异硫氰酸酯或盐
4.如权利要求1或2所述的化合物的用途，其特征在于，用于制备药物、农用化学品、或其中间体。
5.如权利要求4所述的用途，其特征在于，所述的药物、农用化学品、或其中间体是硫代咪唑啉酮。
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102004024011A DE102004024011A1 (de) | 2004-05-14 | 2004-05-14 | Difluorbenzo-1,3-dioxole |
| DE102004024011.6 | 2004-05-14 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1696126A true CN1696126A (zh) | 2005-11-16 |
| CN100569766C CN100569766C (zh) | 2009-12-16 |
Family
ID=34935867
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNB2005100712929A Expired - Fee Related CN100569766C (zh) | 2004-05-14 | 2005-05-11 | 二氟苯并-1,3-间二氧杂环戊烯 |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US7259267B2 (zh) |
| EP (1) | EP1595875B1 (zh) |
| JP (1) | JP5192637B2 (zh) |
| CN (1) | CN100569766C (zh) |
| AT (1) | ATE513824T1 (zh) |
| DE (1) | DE102004024011A1 (zh) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR102080621B1 (ko) | 2015-03-06 | 2020-04-14 | 한온시스템 주식회사 | 전동압축기 및 상기 전동압축기의 유분리기 가공 방법 |
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| JP2020518107A (ja) | 2017-04-26 | 2020-06-18 | オーティーアイ ルミオニクス インコーポレーテッドＯｔｉ Ｌｕｍｉｏｎｉｃｓ Ｉｎｃ． | 表面上のコーティングをパターン化する方法およびパターン化されたコーティングを含むデバイス |
| JP2022532144A (ja) | 2019-05-08 | 2022-07-13 | オーティーアイ ルミオニクス インコーポレーテッド | 核生成抑制コーティングを形成するための材料およびそれを組み込んだデバイス |
| WO2022123431A1 (en) | 2020-12-07 | 2022-06-16 | Oti Lumionics Inc. | Patterning a conductive deposited layer using a nucleation inhibiting coating and an underlying metallic coating |
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| DE3023328A1 (de) * | 1980-06-21 | 1982-01-14 | Bayer Ag, 5090 Leverkusen | Substituierte benzol-(thio)harnstoffe, verfahren zu ihrer herstellung und ihre verwendung als schaedlingsbekaempfungsmittel |
| ZA858002B (en) * | 1984-10-25 | 1987-04-29 | Fmc Corp | Pyrazoline insecticides |
| US4743611A (en) | 1986-07-02 | 1988-05-10 | American Home Products Corp. | Naphthalenylsulfonylimidazolidinediones and their thioxo analogs useful as aldose reductase inhibitors |
| DE4032089A1 (de) | 1990-01-24 | 1991-07-25 | Bayer Ag | Substituierte pyrazolinderivate |
| US5310724A (en) * | 1990-02-09 | 1994-05-10 | Fmc Corporation | Herbicidal substituted phenyl-1,2,4-triazol-5(1H)-thiones |
| DE4133156A1 (de) * | 1991-10-07 | 1993-04-08 | Bayer Ag | Verfahren zur herstellung von fluorsubstituierten aminobenzodioxolen und -benzodioxanen und neue zwischenprodukte |
| US5663189A (en) * | 1993-07-01 | 1997-09-02 | The Procter & Gamble Company | 2-imidazolinylamino heterocyclic compounds useful as alpha-2 adrenoceptor agonists |
| EP1285657A3 (en) * | 1993-10-13 | 2003-08-20 | Allergan, Inc. | Methods for using (2-imidazolin-2-ylamino) quinoxaline derivatives |
| JPH07309831A (ja) * | 1994-05-17 | 1995-11-28 | Sumitomo Chem Co Ltd | イソチオシアネート誘導体の製造法 |
| US6558669B1 (en) * | 1996-08-28 | 2003-05-06 | Immunomedics, Inc. | Stable radioiodine conjugates and methods for their synthesis |
| JP2002519404A (ja) * | 1998-07-07 | 2002-07-02 | スミスクライン・ビーチャム・コーポレイション | 新規蛍光ランタニドキレート |
| FR2823209B1 (fr) * | 2001-04-04 | 2003-12-12 | Fournier Lab Sa | Nouvelles thiohydantoines et leur utilisation en therapeutique |
-
2004
- 2004-05-14 DE DE102004024011A patent/DE102004024011A1/de not_active Withdrawn
-
2005
- 2005-04-28 AT AT05009299T patent/ATE513824T1/de active
- 2005-04-28 EP EP05009299A patent/EP1595875B1/de not_active Not-in-force
- 2005-05-11 US US11/126,534 patent/US7259267B2/en not_active Expired - Fee Related
- 2005-05-11 CN CNB2005100712929A patent/CN100569766C/zh not_active Expired - Fee Related
- 2005-05-12 JP JP2005140200A patent/JP5192637B2/ja not_active Expired - Fee Related
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR102080621B1 (ko) | 2015-03-06 | 2020-04-14 | 한온시스템 주식회사 | 전동압축기 및 상기 전동압축기의 유분리기 가공 방법 |
Also Published As
| Publication number | Publication date |
|---|---|
| DE102004024011A1 (de) | 2005-12-01 |
| JP5192637B2 (ja) | 2013-05-08 |
| EP1595875A3 (de) | 2006-02-08 |
| JP2005325118A (ja) | 2005-11-24 |
| US7259267B2 (en) | 2007-08-21 |
| EP1595875A2 (de) | 2005-11-16 |
| US20050272811A1 (en) | 2005-12-08 |
| CN100569766C (zh) | 2009-12-16 |
| ATE513824T1 (de) | 2011-07-15 |
| EP1595875B1 (de) | 2011-06-22 |
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