UA78876C2 - Process for production of an acetylenic compound - Google Patents

Process for production of an acetylenic compound Download PDF

Info

Publication number: UA78876C2
Authority: UA; Ukraine
Prior art keywords: formula; compound; methyl; nitrofluorobenzene; solvent
Prior art date: 2002-10-18

Application number

UAA200504632A

Other languages

English (en)

Ukrainian (uk)

Original Assignee

Nissan Chemical Ind Ltd

Priority date (The priority date 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 date listed.)

2002-10-18

Filing date

2003-09-26

Publication date

2007-04-25

2003-09-26 Application filed by Nissan Chemical Ind Ltd filed Critical Nissan Chemical Ind Ltd

2007-04-25 Publication of UA78876C2 publication Critical patent/UA78876C2/uk

Links

238000000034 method Methods 0.000 title claims abstract description 34
150000001875 compounds Chemical class 0.000 title claims abstract description 27
238000004519 manufacturing process Methods 0.000 title abstract description 4
WFQDTOYDVUWQMS-UHFFFAOYSA-N 1-fluoro-4-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(F)C=C1 WFQDTOYDVUWQMS-UHFFFAOYSA-N 0.000 claims abstract description 22
-1 2-methyl-3-butyn-2-ol alkoxide Chemical class 0.000 claims description 26
239000002904 solvent Substances 0.000 claims description 26
HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 18
230000003993 interaction Effects 0.000 claims description 2
238000012876 topography Methods 0.000 claims 1
CEBKHWWANWSNTI-UHFFFAOYSA-N 2-methylbut-3-yn-2-ol Chemical compound CC(C)(O)C#C CEBKHWWANWSNTI-UHFFFAOYSA-N 0.000 abstract description 13
150000004703 alkoxides Chemical class 0.000 abstract description 10
239000003814 drug Substances 0.000 abstract 1
229940079593 drug Drugs 0.000 abstract 1
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 39
238000006243 chemical reaction Methods 0.000 description 22
239000012071 phase Substances 0.000 description 18
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
239000012043 crude product Substances 0.000 description 14
239000000203 mixture Substances 0.000 description 13
YMWUJEATGCHHMB-UHFFFAOYSA-N dichloromethane Natural products ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 11
239000000047 product Substances 0.000 description 10
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 9
238000003756 stirring Methods 0.000 description 8
230000015572 biosynthetic process Effects 0.000 description 7
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
239000006227 byproduct Substances 0.000 description 6
BTJIUGUIPKRLHP-UHFFFAOYSA-N 4-nitrophenol Chemical compound OC1=CC=C([N+]([O-])=O)C=C1 BTJIUGUIPKRLHP-UHFFFAOYSA-N 0.000 description 5
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 5
239000003054 catalyst Substances 0.000 description 5
238000004128 high performance liquid chromatography Methods 0.000 description 5
239000002480 mineral oil Substances 0.000 description 5
235000010446 mineral oil Nutrition 0.000 description 5
239000012312 sodium hydride Substances 0.000 description 5
229910000104 sodium hydride Inorganic materials 0.000 description 5
239000000243 solution Substances 0.000 description 5
RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 4
239000002220 antihypertensive agent Substances 0.000 description 4
239000008346 aqueous phase Substances 0.000 description 4
239000003795 chemical substances by application Substances 0.000 description 4
238000001816 cooling Methods 0.000 description 4
229910052751 metal Inorganic materials 0.000 description 4
239000002184 metal Substances 0.000 description 4
230000035484 reaction time Effects 0.000 description 4
239000000126 substance Substances 0.000 description 4
239000000725 suspension Substances 0.000 description 4
238000003786 synthesis reaction Methods 0.000 description 4
MEKOFIRRDATTAG-UHFFFAOYSA-N 2,2,5,8-tetramethyl-3,4-dihydrochromen-6-ol Chemical compound C1CC(C)(C)OC2=C1C(C)=C(O)C=C2C MEKOFIRRDATTAG-UHFFFAOYSA-N 0.000 description 3
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 3
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 3
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
238000004440 column chromatography Methods 0.000 description 3
229910052802 copper Inorganic materials 0.000 description 3
239000010949 copper Substances 0.000 description 3
230000001862 defibrillatory effect Effects 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
238000002360 preparation method Methods 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
239000000741 silica gel Substances 0.000 description 3
229910002027 silica gel Inorganic materials 0.000 description 3
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
230000000052 comparative effect Effects 0.000 description 2
239000013078 crystal Substances 0.000 description 2
238000002425 crystallisation Methods 0.000 description 2
230000008025 crystallization Effects 0.000 description 2
238000002474 experimental method Methods 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
229910001385 heavy metal Inorganic materials 0.000 description 2
229910052744 lithium Inorganic materials 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
239000011734 sodium Substances 0.000 description 2
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
238000005160 1H NMR spectroscopy Methods 0.000 description 1
IQUPABOKLQSFBK-UHFFFAOYSA-N 2-nitrophenol Chemical compound OC1=CC=CC=C1[N+]([O-])=O IQUPABOKLQSFBK-UHFFFAOYSA-N 0.000 description 1
USCSRAJGJYMJFZ-UHFFFAOYSA-N 3-methyl-1-butyne Chemical compound CC(C)C#C USCSRAJGJYMJFZ-UHFFFAOYSA-N 0.000 description 1
DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical group CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 1
KYNSBQPICQTCGU-UHFFFAOYSA-N Benzopyrane Chemical compound C1=CC=C2C=CCOC2=C1 KYNSBQPICQTCGU-UHFFFAOYSA-N 0.000 description 1
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
238000005481 NMR spectroscopy Methods 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 description 1
230000000397 acetylating effect Effects 0.000 description 1
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
230000003440 anti-fibrillation Effects 0.000 description 1
229910052787 antimony Inorganic materials 0.000 description 1
WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
239000002585 base Substances 0.000 description 1
150000001562 benzopyrans Chemical class 0.000 description 1
NDKBVBUGCNGSJJ-UHFFFAOYSA-M benzyltrimethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)CC1=CC=CC=C1 NDKBVBUGCNGSJJ-UHFFFAOYSA-M 0.000 description 1
GBRBMTNGQBKBQE-UHFFFAOYSA-L copper;diiodide Chemical compound I[Cu]I GBRBMTNGQBKBQE-UHFFFAOYSA-L 0.000 description 1
230000007423 decrease Effects 0.000 description 1
238000001514 detection method Methods 0.000 description 1
FAMRKDQNMBBFBR-BQYQJAHWSA-N diethyl azodicarboxylate Substances CCOC(=O)\N=N\C(=O)OCC FAMRKDQNMBBFBR-BQYQJAHWSA-N 0.000 description 1
ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 1
238000004821 distillation Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
239000003480 eluent Substances 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
FAMRKDQNMBBFBR-UHFFFAOYSA-N ethyl n-ethoxycarbonyliminocarbamate Chemical compound CCOC(=O)N=NC(=O)OCC FAMRKDQNMBBFBR-UHFFFAOYSA-N 0.000 description 1
238000000605 extraction Methods 0.000 description 1
238000001914 filtration Methods 0.000 description 1
150000008282 halocarbons Chemical class 0.000 description 1
235000012907 honey Nutrition 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
229910052987 metal hydride Inorganic materials 0.000 description 1
150000004681 metal hydrides Chemical class 0.000 description 1
239000011259 mixed solution Substances 0.000 description 1
239000012046 mixed solvent Substances 0.000 description 1
239000003921 oil Substances 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
230000000704 physical effect Effects 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
229910000105 potassium hydride Inorganic materials 0.000 description 1
238000000746 purification Methods 0.000 description 1
239000012264 purified product Substances 0.000 description 1
230000009257 reactivity Effects 0.000 description 1
230000035945 sensitivity Effects 0.000 description 1
238000010898 silica gel chromatography Methods 0.000 description 1
229910000033 sodium borohydride Inorganic materials 0.000 description 1
239000012279 sodium borohydride Substances 0.000 description 1
SETMGIIITGNLAS-UHFFFAOYSA-N spizofurone Chemical compound O=C1C2=CC(C(=O)C)=CC=C2OC21CC2 SETMGIIITGNLAS-UHFFFAOYSA-N 0.000 description 1
229950001870 spizofurone Drugs 0.000 description 1
239000007858 starting material Substances 0.000 description 1
JABYJIQOLGWMQW-UHFFFAOYSA-N undec-4-ene Chemical compound CCCCCCC=CCCC JABYJIQOLGWMQW-UHFFFAOYSA-N 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C201/00—Preparation of esters of nitric or nitrous acid or of compounds containing nitro or nitroso groups bound to a carbon skeleton
- C07C201/06—Preparation of nitro compounds
- C07C201/12—Preparation of nitro compounds by reactions not involving the formation of nitro groups
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/27—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups
- C07C205/35—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C205/36—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton to carbon atoms of the same non-condensed six-membered aromatic ring or to carbon atoms of six-membered aromatic rings being part of the same condensed ring system
- C07C205/37—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton to carbon atoms of the same non-condensed six-membered aromatic ring or to carbon atoms of six-membered aromatic rings being part of the same condensed ring system the oxygen atom of at least one of the etherified hydroxy groups being further bound to an acyclic carbon atom

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

UAA200504632A 2002-10-18 2003-09-26 Process for production of an acetylenic compound UA78876C2 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
JP2002303876		2002-10-18
PCT/JP2003/012312 WO2004035520A1 (ja)	2002-10-18	2003-09-26	アセチレン化合物の製造方法

Publications (1)

Publication Number	Publication Date
UA78876C2 true UA78876C2 (en)	2007-04-25

Family

ID=32105088

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
UAA200504632A UA78876C2 (en)	2002-10-18	2003-09-26	Process for production of an acetylenic compound

Country Status (16)

Country	Link
US (1)	US7038091B2 (de)
EP (1)	EP1564201A4 (de)
JP (1)	JP4258658B2 (de)
KR (1)	KR101004133B1 (de)
CN (1)	CN1296342C (de)
AU (1)	AU2003268683B2 (de)
CA (1)	CA2502360C (de)
IL (1)	IL168110A (de)
MX (1)	MXPA05004124A (de)
NO (1)	NO331176B1 (de)
NZ (1)	NZ540107A (de)
RU (1)	RU2315747C2 (de)
TW (1)	TWI318972B (de)
UA (1)	UA78876C2 (de)
WO (1)	WO2004035520A1 (de)
ZA (1)	ZA200503239B (de)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JP2006011074A (ja) *	2004-06-25	2006-01-12	Seiko Epson Corp	表示コントローラ、電子機器及び画像データ供給方法
DE102007028925A1 (de)	2007-06-22	2008-12-24	Saltigo Gmbh	Verfahren zur Herstellung von 2-Phenoxyacetalen und den daraus korrespondierenden 2-Phenoxycarbaldehyden
EP3026047A4 (de)	2013-07-25	2017-05-17	Nissan Chemical Industries, Ltd.	Verfahren zur herstellung einer heterocyclischen verbindung

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB1093121A (en) *	1963-05-31	1967-11-29	Wellcome Found	Etherified ªÐ-hydroxyanilines
JPS5811407B2 (ja) *	1979-12-24	1983-03-02	旭化成株式会社	安定化１，１，１−トリクロルエタン組成物
DE3364145D1 (de)	1982-04-08	1986-07-24	Beecham Group Plc	Antihypertensive benzopyranols

2003
- 2003-09-26 EP EP03748596A patent/EP1564201A4/de not_active Withdrawn
- 2003-09-26 UA UAA200504632A patent/UA78876C2/uk unknown
- 2003-09-26 RU RU2005115105/04A patent/RU2315747C2/ru not_active IP Right Cessation
- 2003-09-26 WO PCT/JP2003/012312 patent/WO2004035520A1/ja not_active Ceased
- 2003-09-26 AU AU2003268683A patent/AU2003268683B2/en not_active Ceased
- 2003-09-26 CA CA2502360A patent/CA2502360C/en not_active Expired - Fee Related
- 2003-09-26 JP JP2004544912A patent/JP4258658B2/ja not_active Expired - Fee Related
- 2003-09-26 KR KR1020057006717A patent/KR101004133B1/ko not_active Expired - Fee Related
- 2003-09-26 CN CNB038243326A patent/CN1296342C/zh not_active Expired - Fee Related
- 2003-09-26 US US10/531,458 patent/US7038091B2/en not_active Expired - Fee Related
- 2003-09-26 NZ NZ540107A patent/NZ540107A/en not_active IP Right Cessation
- 2003-09-26 MX MXPA05004124A patent/MXPA05004124A/es active IP Right Grant
- 2003-10-15 TW TW092128576A patent/TWI318972B/zh not_active IP Right Cessation
2005
- 2005-04-18 IL IL168110A patent/IL168110A/en not_active IP Right Cessation
- 2005-04-21 ZA ZA200503239A patent/ZA200503239B/en unknown
- 2005-05-18 NO NO20052392A patent/NO331176B1/no not_active IP Right Cessation

Also Published As

Publication number	Publication date
AU2003268683B2 (en)	2009-09-03
NO20052392D0 (no)	2005-05-18
US20060041031A1 (en)	2006-02-23
MXPA05004124A (es)	2005-06-24
IL168110A (en)	2012-02-29
KR101004133B1 (ko)	2010-12-27
NZ540107A (en)	2006-04-28
IL168110A0 (en)	2009-02-11
AU2003268683A1 (en)	2004-05-04
JPWO2004035520A1 (ja)	2006-02-16
NO20052392L (no)	2005-07-18
JP4258658B2 (ja)	2009-04-30
RU2005115105A (ru)	2006-01-10
CN1296342C (zh)	2007-01-24
US7038091B2 (en)	2006-05-02
WO2004035520A1 (ja)	2004-04-29
EP1564201A4 (de)	2006-11-08
RU2315747C2 (ru)	2008-01-27
TWI318972B (en)	2010-01-01
TW200410930A (en)	2004-07-01
CA2502360C (en)	2011-06-21
KR20050070068A (ko)	2005-07-05
EP1564201A1 (de)	2005-08-17
CN1688536A (zh)	2005-10-26
CA2502360A1 (en)	2004-04-29
ZA200503239B (en)	2006-06-28
NO331176B1 (no)	2011-10-24

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