IL28138A - Resolution of racemic 6-phenyl-2,3,5,6-tetrahydroimidazo(2,1-b)thiazole and recovery of the resolving agent - Google Patents

Resolution of racemic 6-phenyl-2,3,5,6-tetrahydroimidazo(2,1-b)thiazole and recovery of the resolving agent

Info

Publication number: IL28138A
Authority: IL; Israel
Prior art keywords: phenyl; thiazole; tetrahydroimidazo; salt; camphorsulfonate
Prior art date: 1966-08-18

Application number

IL28138A

Other languages

English (en)

Original Assignee

American Cyanamid Co

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.)

1966-08-18

Filing date

1967-06-12

Publication date

1971-03-24

1967-06-12 Application filed by American Cyanamid Co filed Critical American Cyanamid Co

1971-03-24 Publication of IL28138A publication Critical patent/IL28138A/en

Links

238000011084 recovery Methods 0.000 title description 7
HLFSDGLLUJUHTE-UHFFFAOYSA-N 6-phenyl-2,3,5,6-tetrahydroimidazo[2,1-b][1,3]thiazole Chemical compound N1=C2SCCN2CC1C1=CC=CC=C1 HLFSDGLLUJUHTE-UHFFFAOYSA-N 0.000 title 1
FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 37
150000003839 salts Chemical class 0.000 claims description 34
150000001875 compounds Chemical class 0.000 claims description 11
MIOPJNTWMNEORI-ZDFGOMNRSA-N [2,2,3,3,4,5,5-heptadeuterio-7-methyl-6-oxo-7-(trideuteriomethyl)-1-bicyclo[2.2.1]heptanyl]methanesulfonic acid Chemical compound C12(C(=O)C(C(C(C1([2H])[2H])([2H])[2H])(C2(C([2H])([2H])[2H])C)[2H])([2H])[2H])CS(=O)(=O)O MIOPJNTWMNEORI-ZDFGOMNRSA-N 0.000 claims description 10
238000000034 method Methods 0.000 claims description 10
MIOPJNTWMNEORI-GMSGAONNSA-N (S)-camphorsulfonic acid Chemical class C1C[C@@]2(CS(O)(=O)=O)C(=O)C[C@@H]1C2(C)C MIOPJNTWMNEORI-GMSGAONNSA-N 0.000 claims description 6
239000002253 acid Substances 0.000 claims description 3
239000003795 chemical substances by application Substances 0.000 claims description 2
UTCSSFWDNNEEBH-UHFFFAOYSA-N imidazo[1,2-a]pyridine Chemical compound C1=CC=CC2=NC=CN21 UTCSSFWDNNEEBH-UHFFFAOYSA-N 0.000 claims 1
238000001556 precipitation Methods 0.000 claims 1
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 69
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 50
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 26
229960001701 chloroform Drugs 0.000 description 25
239000002904 solvent Substances 0.000 description 20
239000000243 solution Substances 0.000 description 19
230000008018 melting Effects 0.000 description 17
238000002844 melting Methods 0.000 description 17
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
238000001914 filtration Methods 0.000 description 12
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
239000000047 product Substances 0.000 description 11
239000002585 base Substances 0.000 description 10
239000000203 mixture Substances 0.000 description 10
239000012453 solvate Substances 0.000 description 10
239000000706 filtrate Substances 0.000 description 8
150000001412 amines Chemical class 0.000 description 7
230000003287 optical effect Effects 0.000 description 7
238000001704 evaporation Methods 0.000 description 5
229910000041 hydrogen chloride Inorganic materials 0.000 description 5
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 5
239000012452 mother liquor Substances 0.000 description 4
239000002244 precipitate Substances 0.000 description 4
ORECNKBJIMKZNX-UHFFFAOYSA-N 1,3-thiazol-3-ium;chloride Chemical compound Cl.C1=CSC=N1 ORECNKBJIMKZNX-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
HLFSDGLLUJUHTE-SNVBAGLBSA-N Levamisole Chemical compound C1([C@H]2CN3CCSC3=N2)=CC=CC=C1 HLFSDGLLUJUHTE-SNVBAGLBSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
239000013078 crystal Substances 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
MIOPJNTWMNEORI-XVKPBYJWSA-N (R)-camphorsulfonic acid Chemical class C1C[C@]2(CS(O)(=O)=O)C(=O)C[C@H]1C2(C)C MIOPJNTWMNEORI-XVKPBYJWSA-N 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
MIOPJNTWMNEORI-UHFFFAOYSA-N camphorsulfonic acid Chemical class C1CC2(CS(O)(=O)=O)C(=O)CC1C2(C)C MIOPJNTWMNEORI-UHFFFAOYSA-N 0.000 description 2
OSASVXMJTNOKOY-UHFFFAOYSA-N chlorobutanol Chemical compound CC(C)(O)C(Cl)(Cl)Cl OSASVXMJTNOKOY-UHFFFAOYSA-N 0.000 description 2
238000002425 crystallisation Methods 0.000 description 2
230000008025 crystallization Effects 0.000 description 2
230000008020 evaporation Effects 0.000 description 2
239000012535 impurity Substances 0.000 description 2
239000007787 solid Substances 0.000 description 2
239000007858 starting material Substances 0.000 description 2
XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 description 1
230000000507 anthelmentic effect Effects 0.000 description 1
238000009835 boiling Methods 0.000 description 1
239000003610 charcoal Substances 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
229960004926 chlorobutanol Drugs 0.000 description 1
238000001035 drying Methods 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
239000012065 filter cake Substances 0.000 description 1
239000012458 free base Substances 0.000 description 1
231100001231 less toxic Toxicity 0.000 description 1
231100000053 low toxicity Toxicity 0.000 description 1
239000000463 material Substances 0.000 description 1
239000000155 melt Substances 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
239000000376 reactant Substances 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000010414 supernatant solution Substances 0.000 description 1
-1 thiazole acetate salt Chemical class 0.000 description 1
238000010792 warming Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B57/00—Separation of optically-active compounds

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

IL28138A 1966-08-18 1967-06-12 Resolution of racemic 6-phenyl-2,3,5,6-tetrahydroimidazo(2,1-b)thiazole and recovery of the resolving agent IL28138A (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US57318666A	1966-08-18	1966-08-18
US81878369A	1969-04-23	1969-04-23

Publications (1)

Publication Number	Publication Date
IL28138A true IL28138A (en)	1971-03-24

Family

ID=27076047

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL28138A IL28138A (en)	1966-08-18	1967-06-12	Resolution of racemic 6-phenyl-2,3,5,6-tetrahydroimidazo(2,1-b)thiazole and recovery of the resolving agent

Country Status (9)

Country	Link
US (1)	US3565907A (de)
BE (1)	BE702753A (de)
CH (1)	CH501661A (de)
DE (1)	DE1645991C3 (de)
ES (1)	ES344217A1 (de)
GB (1)	GB1127852A (de)
IL (1)	IL28138A (de)
NL (1)	NL6709557A (de)
SE (1)	SE318886B (de)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
USD411495S (en)	1998-03-20	1999-06-29	Elegant USA, Inc.	Steering wheel cover
USD415082S (en)	1998-03-20	1999-10-12	Elegant Usa, Llc	Steering wheel cover
USD415459S (en)	1998-03-20	1999-10-19	Elegant Usa, Llc	Steering wheel cover

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4153678A (en) *	1978-07-17	1979-05-08	American Cyanamid Company	Levamisole effervescent tablets

1967
- 1967-06-12 IL IL28138A patent/IL28138A/en unknown
- 1967-06-13 GB GB27303/67A patent/GB1127852A/en not_active Expired
- 1967-06-22 SE SE9009/67A patent/SE318886B/xx unknown
- 1967-07-10 NL NL6709557A patent/NL6709557A/xx unknown
- 1967-08-17 BE BE702753D patent/BE702753A/xx unknown
- 1967-08-18 DE DE1645991A patent/DE1645991C3/de not_active Expired
- 1967-08-18 ES ES344217A patent/ES344217A1/es not_active Expired
- 1967-08-18 CH CH1165767A patent/CH501661A/de not_active IP Right Cessation
1969
- 1969-04-23 US US818783A patent/US3565907A/en not_active Expired - Lifetime

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
USD411495S (en)	1998-03-20	1999-06-29	Elegant USA, Inc.	Steering wheel cover
USD415082S (en)	1998-03-20	1999-10-12	Elegant Usa, Llc	Steering wheel cover
USD415459S (en)	1998-03-20	1999-10-19	Elegant Usa, Llc	Steering wheel cover

Also Published As

Publication number	Publication date
DE1645991A1 (de)	1971-01-21
CH501661A (de)	1971-01-15
DE1645991B2 (de)	1977-09-22
ES344217A1 (es)	1968-12-16
GB1127852A (en)	1968-09-18
BE702753A (de)	1968-02-19
SE318886B (de)	1969-12-22
DE1645991C3 (de)	1978-05-24
US3565907A (en)	1971-02-23
NL6709557A (de)	1968-02-19

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