KR100859386B1 - 티오펜의 클로로메틸화 반응 - Google Patents
티오펜의 클로로메틸화 반응 Download PDFInfo
- Publication number
- KR100859386B1 KR100859386B1 KR1020037015114A KR20037015114A KR100859386B1 KR 100859386 B1 KR100859386 B1 KR 100859386B1 KR 1020037015114 A KR1020037015114 A KR 1020037015114A KR 20037015114 A KR20037015114 A KR 20037015114A KR 100859386 B1 KR100859386 B1 KR 100859386B1
- Authority
- KR
- South Korea
- Prior art keywords
- ketone
- formula
- methyl
- thiophene
- compound
- Prior art date
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- 229930192474 thiophene Natural products 0.000 title claims abstract description 25
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 title claims description 46
- 238000007265 chloromethylation reaction Methods 0.000 title claims description 12
- 150000001875 compounds Chemical class 0.000 claims abstract description 48
- 238000000034 method Methods 0.000 claims abstract description 26
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 38
- 239000000203 mixture Substances 0.000 claims description 16
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical group CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 15
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 12
- 239000011541 reaction mixture Substances 0.000 claims description 12
- 239000007789 gas Substances 0.000 claims description 11
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 claims description 9
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 claims description 9
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 9
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims description 9
- 229940043265 methyl isobutyl ketone Drugs 0.000 claims description 9
- 229930040373 Paraformaldehyde Natural products 0.000 claims description 6
- 229920002866 paraformaldehyde Polymers 0.000 claims description 6
- ZPVFWPFBNIEHGJ-UHFFFAOYSA-N 2-octanone Chemical compound CCCCCCC(C)=O ZPVFWPFBNIEHGJ-UHFFFAOYSA-N 0.000 claims description 4
- HCFAJYNVAYBARA-UHFFFAOYSA-N 4-heptanone Chemical compound CCCC(=O)CCC HCFAJYNVAYBARA-UHFFFAOYSA-N 0.000 claims description 4
- CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 229940032007 methylethyl ketone Drugs 0.000 claims description 4
- XNLICIUVMPYHGG-UHFFFAOYSA-N pentan-2-one Chemical compound CCCC(C)=O XNLICIUVMPYHGG-UHFFFAOYSA-N 0.000 claims description 4
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 claims description 4
- 238000000926 separation method Methods 0.000 claims description 4
- -1 - (C 1 -C 6 ) alkyl ketone Chemical class 0.000 claims description 3
- QQZOPKMRPOGIEB-UHFFFAOYSA-N 2-Oxohexane Chemical compound CCCCC(C)=O QQZOPKMRPOGIEB-UHFFFAOYSA-N 0.000 claims description 2
- 239000003444 phase transfer catalyst Substances 0.000 claims description 2
- PJGSXYOJTGTZAV-UHFFFAOYSA-N pinacolone Chemical compound CC(=O)C(C)(C)C PJGSXYOJTGTZAV-UHFFFAOYSA-N 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims 4
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims 1
- 239000003513 alkali Substances 0.000 claims 1
- 229910017053 inorganic salt Inorganic materials 0.000 claims 1
- 238000001179 sorption measurement Methods 0.000 claims 1
- FUOHKPSBGLXIRL-UHFFFAOYSA-N 2-(chloromethyl)thiophene Chemical compound ClCC1=CC=CS1 FUOHKPSBGLXIRL-UHFFFAOYSA-N 0.000 abstract description 10
- 125000000468 ketone group Chemical group 0.000 abstract description 8
- 239000000543 intermediate Substances 0.000 abstract description 3
- 150000003577 thiophenes Chemical class 0.000 abstract description 2
- 239000004480 active ingredient Substances 0.000 abstract 1
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 12
- 239000000243 solution Substances 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 239000000047 product Substances 0.000 description 7
- CLSHQIDDCJTHAJ-UHFFFAOYSA-N 2-thienylacetonitrile Chemical compound N#CCC1=CC=CS1 CLSHQIDDCJTHAJ-UHFFFAOYSA-N 0.000 description 5
- KKWWFYAKOFXBEY-UHFFFAOYSA-N 3-(chloromethyl)thiophene Chemical compound ClCC=1C=CSC=1 KKWWFYAKOFXBEY-UHFFFAOYSA-N 0.000 description 5
- 239000008186 active pharmaceutical agent Substances 0.000 description 5
- 239000012074 organic phase Substances 0.000 description 5
- 239000012535 impurity Substances 0.000 description 4
- 230000007935 neutral effect Effects 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000005292 vacuum distillation Methods 0.000 description 3
- OJBWNBCXVFAMEX-UHFFFAOYSA-N 2,5-bis(chloromethyl)thiophene Chemical compound ClCC1=CC=C(CCl)S1 OJBWNBCXVFAMEX-UHFFFAOYSA-N 0.000 description 2
- JOIVULVUCVIERM-UHFFFAOYSA-N 2-(2-chloro-1-thiophen-2-ylethyl)thiophene Chemical compound C=1C=CSC=1C(CCl)C1=CC=CS1 JOIVULVUCVIERM-UHFFFAOYSA-N 0.000 description 2
- JZSRHKOFXIACDX-UHFFFAOYSA-N 2-(thiophen-2-ylmethyl)thiophene Chemical compound C=1C=CSC=1CC1=CC=CS1 JZSRHKOFXIACDX-UHFFFAOYSA-N 0.000 description 2
- GWZCLMWEJWPFFA-UHFFFAOYSA-N 2-thiophen-3-ylacetonitrile Chemical compound N#CCC=1C=CSC=1 GWZCLMWEJWPFFA-UHFFFAOYSA-N 0.000 description 2
- SYBYTAAJFKOIEJ-UHFFFAOYSA-N 3-Methylbutan-2-one Chemical compound CC(C)C(C)=O SYBYTAAJFKOIEJ-UHFFFAOYSA-N 0.000 description 2
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 2
- 239000000178 monomer Chemical group 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- CXRPNLIUCUKLPK-UHFFFAOYSA-N 2-(1-thiophen-2-ylethyl)thiophene Chemical compound C=1C=CSC=1C(C)C1=CC=CS1 CXRPNLIUCUKLPK-UHFFFAOYSA-N 0.000 description 1
- HVLUYXIJZLDNIS-UHFFFAOYSA-N 2-thiophen-2-ylethanamine Chemical compound NCCC1=CC=CS1 HVLUYXIJZLDNIS-UHFFFAOYSA-N 0.000 description 1
- RZUXCXVPQXRSCO-UHFFFAOYSA-N 3-methyl-2-(2-methylpropyl)thiophene Chemical compound CC(C)CC=1SC=CC=1C RZUXCXVPQXRSCO-UHFFFAOYSA-N 0.000 description 1
- PVCCGWFSEUKWBA-UHFFFAOYSA-N 5-(chloromethyl)-4-methylthiophen-2-ol Chemical compound CC=1C=C(O)SC=1CCl PVCCGWFSEUKWBA-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001412 amines Chemical group 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000000593 degrading effect Effects 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 230000009977 dual effect Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 239000002360 explosive Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 230000002452 interceptive effect Effects 0.000 description 1
- 238000011031 large-scale manufacturing process Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 210000004400 mucous membrane Anatomy 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- YBRBMKDOPFTVDT-UHFFFAOYSA-O tert-butylammonium Chemical compound CC(C)(C)[NH3+] YBRBMKDOPFTVDT-UHFFFAOYSA-O 0.000 description 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
- WZMPOCLULGAHJR-UHFFFAOYSA-N thiophen-2-ol Chemical compound OC1=CC=CS1 WZMPOCLULGAHJR-UHFFFAOYSA-N 0.000 description 1
- ZPHGMBGIFODUMF-UHFFFAOYSA-N thiophen-2-ylmethanol Chemical compound OCC1=CC=CS1 ZPHGMBGIFODUMF-UHFFFAOYSA-N 0.000 description 1
- HERSKCAGZCXYMC-UHFFFAOYSA-N thiophen-3-ol Chemical compound OC=1C=CSC=1 HERSKCAGZCXYMC-UHFFFAOYSA-N 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/12—Radicals substituted by halogen atoms or nitro or nitroso radicals
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Control Of Charge By Means Of Generators (AREA)
Abstract
Description
Claims (14)
- 제 1항에 있어서, 상기 디-(C1-C6)알킬케톤 용매가 디메틸-케톤, 디에틸-케톤, 디프로필-케톤, 메틸-에틸-케톤, 메틸-프로필-케톤, 메틸-이소프로필-케톤, 메틸-부틸-케톤, 메틸-이소부틸-케톤, 메틸-3차-부틸-케톤, 메틸-펜틸-케톤 및 메틸-헥실-케톤 및 그들의 혼합물로부터 선택됨을 특징으로 하는 방법.
- 제 2항에 있어서, 클로로메틸화 반응이 디메틸-케톤 또는 메틸-에틸-케톤 또는 메틸-이소부틸-케톤 중에서 실시됨을 특징으로 하는 방법.
- 제 1항에 있어서, 클로로메틸화 반응이 -15 내지 +20℃에서 실시됨을 특징으로 하는 방법.
- 제 1항에 있어서, 클로로메틸화 반응이 진한 염산 수용액, 염화수소 가스 및 파라포름알데히드를 사용하여 실시됨을 특징으로 하는 방법.
- 제 5항에 있어서, 무수 염화수소 가스가 반응 혼합물에 도입되거나, 디-(C1-C6)알킬케톤 용매 중에서 흡착시킨 후에 사용됨을 특징으로 하는 방법.
- 제 5항에 있어서, 티오펜, 염산 수용액, 염화수소 가스 및 파라포름알데히드의 몰비가 1.0: 1.0-1.3: 0.75-1.0: 1.0임을 특징으로 하는 방법.
- 제 1항에 있어서, 1 부피 단위의 티오펜으로 계산된 1 내지 3의 부피 단위의 디-(C1-C6)알킬케톤 용매가 사용됨을 특징으로 하는 방법.
- 제 5항에 있어서, 무기 염이 사용된 염화수소 수용액에 용해됨을 특징으로 하는 방법.
- 제 1항에 있어서, 형성된 화학식 (I)의 화합물이 분리되지 않고 화학식 (II) 의 화합물로 추가로 변형됨을 특징으로 하는 방법.
- 제 9항에 있어서, 화학식 (I)의 수득된 화합물이 상 전달 촉매의 존재 또는 부재하에서 알칼리 시아나이드 수용액을 사용함으로써 화학식 (II)의 화합물로 변형됨을 특징으로 하는 방법.
- 삭제
- 삭제
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
HUP0102118 | 2001-05-22 | ||
HU0102118A HU0102118D0 (en) | 2001-05-22 | 2001-05-22 | Process for chloromethylation |
PCT/HU2002/000042 WO2002094806A1 (en) | 2001-05-22 | 2002-05-16 | Chloromethylation of thiophene |
Publications (2)
Publication Number | Publication Date |
---|---|
KR20040018373A KR20040018373A (ko) | 2004-03-03 |
KR100859386B1 true KR100859386B1 (ko) | 2008-09-22 |
Family
ID=89979350
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
KR1020037015114A KR100859386B1 (ko) | 2001-05-22 | 2002-05-16 | 티오펜의 클로로메틸화 반응 |
Country Status (20)
Country | Link |
---|---|
US (1) | US7462725B2 (ko) |
EP (1) | EP1392672B1 (ko) |
JP (1) | JP4467890B2 (ko) |
KR (1) | KR100859386B1 (ko) |
CN (1) | CN1260224C (ko) |
AT (1) | ATE294790T1 (ko) |
BR (1) | BRPI0209874B1 (ko) |
CA (1) | CA2447440C (ko) |
CZ (1) | CZ301166B6 (ko) |
DE (1) | DE60204014T2 (ko) |
DK (1) | DK1392672T3 (ko) |
ES (1) | ES2240738T3 (ko) |
HR (1) | HRP20031068B1 (ko) |
HU (1) | HU0102118D0 (ko) |
MX (1) | MXPA03010594A (ko) |
PL (1) | PL210713B1 (ko) |
PT (1) | PT1392672E (ko) |
SI (1) | SI1392672T1 (ko) |
SK (1) | SK285681B6 (ko) |
WO (1) | WO2002094806A1 (ko) |
Families Citing this family (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN104513225A (zh) * | 2013-10-08 | 2015-04-15 | 华东师范大学 | 2-噻吩乙腈的制备方法 |
CN103880741A (zh) * | 2014-02-28 | 2014-06-25 | 安徽国星生物化学有限公司 | 一种2-氯甲基-3,5-二甲基-4-烷氧基吡啶-n-氧化物的制备方法 |
CN103992302A (zh) * | 2014-06-16 | 2014-08-20 | 商丘凯瑞达化工有限公司 | 2-噻吩乙酸合成工艺 |
CN104327040A (zh) * | 2014-10-11 | 2015-02-04 | 华东师范大学 | 一种2-噻吩乙酸的合成方法 |
US10450512B2 (en) * | 2016-02-10 | 2019-10-22 | Primus Green Energy Inc. | Single-loop octane enrichment |
CN113896709B (zh) * | 2021-11-22 | 2023-02-28 | 南京一苇医药科技有限公司 | 一种苯并噻吩-3-乙酸的合成方法 |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2527680A (en) * | 1945-06-21 | 1950-10-31 | Monsanto Chemicals | Alpha thenyl chloride from hydrogen chloride-formaldehyde solution and thiophene |
US4501903A (en) * | 1983-07-05 | 1985-02-26 | Stauffer Chemical Company | Chloromethylation process |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB639438A (en) * | 1948-02-25 | 1950-06-28 | Ici Ltd | Preparation of organic nitriles |
FR2608607B1 (fr) * | 1986-12-23 | 1989-04-28 | Sanofi Sa | Procede de preparation de thienylethylamines et dithienylethylamines ainsi obtenues |
PL158225B1 (en) * | 1989-06-09 | 1992-08-31 | Method for manufacturing 2-chlormethylthiopen |
-
2001
- 2001-05-22 HU HU0102118A patent/HU0102118D0/hu unknown
-
2002
- 2002-05-16 CA CA2447440A patent/CA2447440C/en not_active Expired - Lifetime
- 2002-05-16 EP EP02727810A patent/EP1392672B1/en not_active Expired - Lifetime
- 2002-05-16 JP JP2002591479A patent/JP4467890B2/ja not_active Expired - Fee Related
- 2002-05-16 KR KR1020037015114A patent/KR100859386B1/ko active IP Right Grant
- 2002-05-16 BR BRPI0209874A patent/BRPI0209874B1/pt not_active IP Right Cessation
- 2002-05-16 US US10/478,238 patent/US7462725B2/en not_active Expired - Lifetime
- 2002-05-16 PL PL363923A patent/PL210713B1/pl unknown
- 2002-05-16 SI SI200230143T patent/SI1392672T1/xx unknown
- 2002-05-16 PT PT02727810T patent/PT1392672E/pt unknown
- 2002-05-16 ES ES02727810T patent/ES2240738T3/es not_active Expired - Lifetime
- 2002-05-16 MX MXPA03010594A patent/MXPA03010594A/es active IP Right Grant
- 2002-05-16 CN CNB028103882A patent/CN1260224C/zh not_active Expired - Lifetime
- 2002-05-16 SK SK1354-2003A patent/SK285681B6/sk not_active IP Right Cessation
- 2002-05-16 AT AT02727810T patent/ATE294790T1/de active
- 2002-05-16 CZ CZ20032973A patent/CZ301166B6/cs not_active IP Right Cessation
- 2002-05-16 WO PCT/HU2002/000042 patent/WO2002094806A1/en active IP Right Grant
- 2002-05-16 DK DK02727810T patent/DK1392672T3/da active
- 2002-05-16 DE DE60204014T patent/DE60204014T2/de not_active Expired - Lifetime
-
2003
- 2003-12-19 HR HR20031068A patent/HRP20031068B1/xx not_active IP Right Cessation
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2527680A (en) * | 1945-06-21 | 1950-10-31 | Monsanto Chemicals | Alpha thenyl chloride from hydrogen chloride-formaldehyde solution and thiophene |
US4501903A (en) * | 1983-07-05 | 1985-02-26 | Stauffer Chemical Company | Chloromethylation process |
Non-Patent Citations (2)
Title |
---|
US 2527680 A. |
US 4501903 A.* |
Also Published As
Publication number | Publication date |
---|---|
SK285681B6 (sk) | 2007-06-07 |
CA2447440C (en) | 2010-10-19 |
PL363923A1 (en) | 2004-11-29 |
PT1392672E (pt) | 2005-08-31 |
CN1511148A (zh) | 2004-07-07 |
HU0102118D0 (en) | 2001-07-30 |
DE60204014D1 (de) | 2005-06-09 |
KR20040018373A (ko) | 2004-03-03 |
CZ20032973A3 (en) | 2004-03-17 |
ATE294790T1 (de) | 2005-05-15 |
MXPA03010594A (es) | 2004-04-02 |
BRPI0209874B1 (pt) | 2016-03-22 |
US20060161008A1 (en) | 2006-07-20 |
BR0209874A (pt) | 2004-06-08 |
CN1260224C (zh) | 2006-06-21 |
EP1392672B1 (en) | 2005-05-04 |
CA2447440A1 (en) | 2002-11-28 |
ES2240738T3 (es) | 2005-10-16 |
DE60204014T2 (de) | 2006-02-02 |
DK1392672T3 (da) | 2005-08-29 |
SI1392672T1 (en) | 2005-10-31 |
CZ301166B6 (cs) | 2009-11-25 |
HRP20031068A2 (en) | 2004-04-30 |
WO2002094806A1 (en) | 2002-11-28 |
HRP20031068B1 (en) | 2011-12-31 |
SK13542003A3 (sk) | 2004-07-07 |
US7462725B2 (en) | 2008-12-09 |
JP4467890B2 (ja) | 2010-05-26 |
PL210713B1 (pl) | 2012-02-29 |
EP1392672A1 (en) | 2004-03-03 |
JP2004532247A (ja) | 2004-10-21 |
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