NL7906109A - Werkwijze voor de bereiding van 4-(5)hydroxyl-5-(4) lager alkyl-imidazolen en hun zuur-additiezouten. - Google Patents

Werkwijze voor de bereiding van 4-(5)hydroxyl-5-(4) lager alkyl-imidazolen en hun zuur-additiezouten. Download PDF

Info

Publication number: NL7906109A
Authority: NL; Netherlands
Prior art keywords: base; process according; preparation; lower alkyl; formula
Prior art date: 1978-08-30

Application number

NL7906109A

Other languages

English (en)

Dutch (nl)

Original Assignee

Delalande Sa

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.)

1978-08-30

Filing date

1979-08-09

Publication date

1980-03-04

1979-08-09 Application filed by Delalande Sa filed Critical Delalande Sa

1980-03-04 Publication of NL7906109A publication Critical patent/NL7906109A/nl

Links

238000000034 method Methods 0.000 title claims description 23
230000008569 process Effects 0.000 title claims description 13
150000003839 salts Chemical class 0.000 title description 12
238000002360 preparation method Methods 0.000 title description 8
239000002253 acid Substances 0.000 title description 5
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 27
150000001875 compounds Chemical class 0.000 claims description 21
239000002585 base Substances 0.000 claims description 20
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 18
238000006243 chemical reaction Methods 0.000 claims description 17
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 12
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 11
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 11
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 11
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 9
SQYNKIJPMDEDEG-UHFFFAOYSA-N paraldehyde Chemical compound CC1OC(C)OC(C)O1 SQYNKIJPMDEDEG-UHFFFAOYSA-N 0.000 claims description 8
229960003868 paraldehyde Drugs 0.000 claims description 8
239000002904 solvent Substances 0.000 claims description 8
150000003512 tertiary amines Chemical class 0.000 claims description 6
150000001298 alcohols Chemical class 0.000 claims description 2
229910052783 alkali metal Inorganic materials 0.000 claims description 2
125000004432 carbon atom Chemical group C* 0.000 claims description 2
150000007529 inorganic bases Chemical class 0.000 claims description 2
150000007530 organic bases Chemical class 0.000 claims description 2
125000001453 quaternary ammonium group Chemical group 0.000 claims description 2
235000019441 ethanol Nutrition 0.000 claims 3
150000001340 alkali metals Chemical class 0.000 claims 1
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
XLSZMDLNRCVEIJ-UHFFFAOYSA-N 4-methylimidazole Chemical compound CC1=CNC=N1 XLSZMDLNRCVEIJ-UHFFFAOYSA-N 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
-1 alkyl imidazoles Chemical class 0.000 description 5
238000002425 crystallisation Methods 0.000 description 4
230000008025 crystallization Effects 0.000 description 4
239000000543 intermediate Substances 0.000 description 4
239000002244 precipitate Substances 0.000 description 4
239000000243 solution Substances 0.000 description 4
239000000203 mixture Substances 0.000 description 3
230000009467 reduction Effects 0.000 description 3
229940086542 triethylamine Drugs 0.000 description 3
230000009471 action Effects 0.000 description 2
125000000217 alkyl group Chemical group 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
230000006872 improvement Effects 0.000 description 2
229940075930 picrate Drugs 0.000 description 2
OXNIZHLAWKMVMX-UHFFFAOYSA-M picrate anion Chemical compound [O-]C1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-M 0.000 description 2
238000000746 purification Methods 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
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 1
230000002378 acidificating effect Effects 0.000 description 1
125000003158 alcohol group Chemical group 0.000 description 1
239000003699 antiulcer agent Substances 0.000 description 1
230000008901 benefit Effects 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
239000003638 chemical reducing agent Substances 0.000 description 1
AQIXAKUUQRKLND-UHFFFAOYSA-N cimetidine Chemical compound N#C/N=C(/NC)NCCSCC=1N=CNC=1C AQIXAKUUQRKLND-UHFFFAOYSA-N 0.000 description 1
229960001380 cimetidine Drugs 0.000 description 1
239000012043 crude product Substances 0.000 description 1
230000007423 decrease Effects 0.000 description 1
229940079593 drug Drugs 0.000 description 1
239000003814 drug Substances 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
239000012535 impurity Substances 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
150000003138 primary alcohols Chemical class 0.000 description 1
239000000047 product Substances 0.000 description 1
230000002035 prolonged effect Effects 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
238000001577 simple distillation Methods 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
239000007787 solid Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/64—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms, e.g. histidine

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

NL7906109A 1978-08-30 1979-08-09 Werkwijze voor de bereiding van 4-(5)hydroxyl-5-(4) lager alkyl-imidazolen en hun zuur-additiezouten. NL7906109A (nl)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
FR7825051A FR2434807A1 (fr)	1978-08-30	1978-08-30	Procede perfectionne de preparation d'hydroxymethyl-4(5) alkyl inferieur-5 (4)-imidazoles et de leurs sels d'addition d'acide
FR7825051		1978-08-30

Publications (1)

Publication Number	Publication Date
NL7906109A true NL7906109A (nl)	1980-03-04

Family

ID=9212212

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NL7906109A NL7906109A (nl)	1978-08-30	1979-08-09	Werkwijze voor de bereiding van 4-(5)hydroxyl-5-(4) lager alkyl-imidazolen en hun zuur-additiezouten.

Country Status (13)

Country	Link
US (1)	US4275216A (fr)
JP (1)	JPS5535075A (fr)
AT (1)	AT373245B (fr)
BE (1)	BE878490A (fr)
DE (1)	DE2934925A1 (fr)
FR (1)	FR2434807A1 (fr)
GB (1)	GB2029414B (fr)
IL (1)	IL58130A (fr)
IT (1)	IT1122746B (fr)
LU (1)	LU81636A1 (fr)
NL (1)	NL7906109A (fr)
SE (1)	SE7907188L (fr)
YU (1)	YU204279A (fr)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE2908212A1 (de) *	1979-03-02	1980-09-11	Basf Ag	Verfahren zur herstellung von 5-hydroxymethylimidazolen
IL75063A (en) *	1985-05-01	1989-03-31	Teva Pharma	Preparation of 4(5)-hydroxymethyl-5(4)-methylimidazole
DE3534083A1 (de) *	1985-09-25	1987-04-02	Basf Ag	Verfahren zur herstellung von hydroximethylimidazolen
CA2165138A1 (fr) *	1995-12-13	1997-06-14	K.S. Keshava Murthy	Methode de preparation du 4-methyl-5-hydroxymethylimidazole

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4104473A (en) *	1976-04-23	1978-08-01	Shikoku Chemicals Corporation	Novel imidazole compounds and process for preparations thereof
ES477086A1 (es) *	1978-04-07	1979-12-16	Eprova Ag	Procedimiento para la preparacion de 4-metil-5-hidroximetil-imidazol.

1978
- 1978-08-30 FR FR7825051A patent/FR2434807A1/fr active Granted
1979
- 1979-07-31 US US06/062,501 patent/US4275216A/en not_active Expired - Lifetime
- 1979-08-09 IT IT25028/79A patent/IT1122746B/it active
- 1979-08-09 NL NL7906109A patent/NL7906109A/nl not_active Application Discontinuation
- 1979-08-21 YU YU02042/79A patent/YU204279A/xx unknown
- 1979-08-23 AT AT0566479A patent/AT373245B/de not_active IP Right Cessation
- 1979-08-28 JP JP10961479A patent/JPS5535075A/ja active Pending
- 1979-08-28 LU LU81636A patent/LU81636A1/fr unknown
- 1979-08-28 IL IL58130A patent/IL58130A/xx unknown
- 1979-08-29 GB GB7929945A patent/GB2029414B/en not_active Expired
- 1979-08-29 SE SE7907188A patent/SE7907188L/xx not_active Application Discontinuation
- 1979-08-29 DE DE19792934925 patent/DE2934925A1/de not_active Withdrawn
- 1979-08-29 BE BE0/196929A patent/BE878490A/fr not_active IP Right Cessation

Also Published As

Publication number	Publication date
AT373245B (de)	1983-12-27
BE878490A (fr)	1980-02-29
US4275216A (en)	1981-06-23
FR2434807B1 (fr)	1981-03-06
ATA566479A (de)	1983-05-15
YU204279A (en)	1983-01-21
GB2029414B (en)	1983-01-12
IT7925028A0 (it)	1979-08-09
FR2434807A1 (fr)	1980-03-28
GB2029414A (en)	1980-03-19
DE2934925A1 (de)	1980-03-13
SE7907188L (sv)	1980-03-01
IL58130A (en)	1983-09-30
IL58130A0 (en)	1979-12-30
IT1122746B (it)	1986-04-23
LU81636A1 (fr)	1981-03-24
JPS5535075A (en)	1980-03-11

Legal Events

Date	Code	Title
1983-03-01	BA	A request for search or an international-type search has been filed
1983-03-01	BB	A search report has been drawn up
1983-11-01	BC	A request for examination has been filed
1985-01-01	A85	Still pending on 85-01-01
1985-04-01	BV	The patent application has lapsed

Publication	Publication Date	Title
JP2515427B2 (ja)	1996-07-10	プレウロムチリン類
NL7906109A (nl)	1980-03-04	Werkwijze voor de bereiding van 4-(5)hydroxyl-5-(4) lager alkyl-imidazolen en hun zuur-additiezouten.
US4380632A (en)	1983-04-19	Method of preparing quinolines, naphthyridines and other nitrogen bi-heterocyclic compounds
KR910004134B1 (ko)	1991-06-22	시클로헥산디온 유도체의 제조방법
HU200446B (en)	1990-06-28	Process for production of 1-alkyl-5-nitro-imidasoles
US4772711A (en)	1988-09-20	Method for the preparation of 3-aminoacrylic acid esters
CA2204964A1 (fr)	1997-11-22	Methode pour la preparation de 3-aminocrotonates substitues
NL9001786A (nl)	1992-03-02	Werkwijze voor de bereiding van gesubstitueerde pyridines via 1-aza-1,3-butadienen en de tussenprodukten 1-aza-1,3-butadienen.
US3689502A (en)	1972-09-05	Preparation of n-(2-alkylthioethyl) nitroimidazoles
US4564696A (en)	1986-01-14	Process for the production of 4-alkoxyacetoacetic acid esters
US4384118A (en)	1983-05-17	4-(3-Iodopropargyloxy) pyrimidine derivatives
HU177508B (en)	1981-10-28	Process for preparing 4-/hydroxymethyl/-imidazoles
US2948725A (en)	1960-08-09	Flow sheet-process
US5777154A (en)	1998-07-07	Method for preparing 3-amino substituted crotonates
JP3031279B2 (ja)	2000-04-10	２−アルコキシ−６−（トリフルオロメチル）ピリミジン−４−オルの製造方法
HU208676B (en)	1993-12-28	Process for producing 1-hydroxyalkyl-5-nitroimidazoles
US4540808A (en)	1985-09-10	Process for the preparation of 4-alkoxyacetoacetic acid ester
US2931811A (en)	1960-04-05	3, 4, 6-trioxo hexahydropyridazine compounds and a process of making same
JPS638351A (ja)	1988-01-14	光学活性α−フエノキシプロピオン酸およびその誘導体のラセミ化法
EP0066440B1 (fr)	1985-07-31	Procédé chimique
JPH08503939A (ja)	1996-04-30	α−アリール‐γ‐ブチロラクトンの製造方法
HUT63396A (en)	1993-08-30	Method for producing 4,6-dialkoxi-pyrimidine derivatives
CN1035672C (zh)	1997-08-20	3－(甲基咪唑基)－甲基－四氢－咔唑酮新的制备方法
KR830002349B1 (ko)	1983-10-24	4-(5)-하이드록시메틸 5(4)-저급알킬이미다졸류의 제조방법
US4459407A (en)	1984-07-10	1-(4-Aminobenzyl)-2,3-dioxopiperazine derivatives and salts thereof