ES477646A1 - Novel method of preparing thiazole derivative - Google Patents
Novel method of preparing thiazole derivativeInfo
- Publication number
- ES477646A1 ES477646A1 ES477646A ES477646A ES477646A1 ES 477646 A1 ES477646 A1 ES 477646A1 ES 477646 A ES477646 A ES 477646A ES 477646 A ES477646 A ES 477646A ES 477646 A1 ES477646 A1 ES 477646A1
- Authority
- ES
- Spain
- Prior art keywords
- formula
- compound
- novel
- halogenoethylisothiocyanate
- alkoxy
- Prior art date
- Legal status (The legal status 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 status listed.)
- Expired
Links
- 150000007979 thiazole derivatives Chemical class 0.000 title abstract 3
- 238000000034 method Methods 0.000 title abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 3
- 239000002253 acid Substances 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 229910052736 halogen Inorganic materials 0.000 abstract 2
- 125000005843 halogen group Chemical group 0.000 abstract 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 abstract 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 abstract 1
- 125000005277 alkyl imino group Chemical group 0.000 abstract 1
- 229940121363 anti-inflammatory agent Drugs 0.000 abstract 1
- 239000002260 anti-inflammatory agent Substances 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 125000001841 imino group Chemical group [H]N=* 0.000 abstract 1
- ZBKFYXZXZJPWNQ-UHFFFAOYSA-N isothiocyanate group Chemical group [N-]=C=S ZBKFYXZXZJPWNQ-UHFFFAOYSA-N 0.000 abstract 1
- 229910000027 potassium carbonate Inorganic materials 0.000 abstract 1
- DNXIASIHZYFFRO-UHFFFAOYSA-N pyrazoline Chemical class C1CN=NC1 DNXIASIHZYFFRO-UHFFFAOYSA-N 0.000 abstract 1
- 239000012312 sodium hydride Substances 0.000 abstract 1
- 229910000104 sodium hydride Inorganic materials 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/08—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D277/12—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D277/14—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/08—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D277/12—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D277/16—Sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D277/34—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D277/36—Sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D277/38—Nitrogen atoms
- C07D277/42—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
PURPOSE:Thiazole derivatives having a substituent in the 2-position useful for preparation of an anti-inflammatory agent and others are derived from a novel compound of 1-alkoxy-2-halogenoethylisothiocyanate in high yield. CONSTITUTION:The reaction of novel 1-alkoxy-2-halogenoethylisothiocyanate of formula I (X is halogen R is alkyl) with a compound of formula II (R' is alkyl, phenyl, substituted phenyl A is O, S, imino, alkylimino) is effected in the presence of an acid acceptor, preferably sodium hydride or potassium carbonate to give a diazoline derivative of formula III. Then the dealcoholation of the product is conducted in the presence of a catalyst amount of an acid to produce said thiazole derivative of formula IV. These procedures may be continuously carried out. The novel compound of formula I is prepared by introducing an isothiocyanate group into a compound of formula V (Y is halogen).
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1612778A JPS54109969A (en) | 1978-02-14 | 1978-02-14 | Novel method of preparing thiazole derivative |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES477646A1 true ES477646A1 (en) | 1979-10-16 |
Family
ID=11907826
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES477646A Expired ES477646A1 (en) | 1978-02-14 | 1979-02-13 | Novel method of preparing thiazole derivative |
Country Status (9)
| Country | Link |
|---|---|
| JP (1) | JPS54109969A (en) |
| AR (1) | AR221715A1 (en) |
| CA (1) | CA1116609A (en) |
| CH (1) | CH639963A5 (en) |
| DK (1) | DK60979A (en) |
| ES (1) | ES477646A1 (en) |
| IT (1) | IT1113001B (en) |
| SE (1) | SE437987B (en) |
| ZA (1) | ZA79673B (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3708201A1 (en) * | 1987-03-13 | 1988-09-22 | Bayer Ag | NEW THIAZOLYL ETHER AND THIOETHER DERIVATIVES |
| DE19548417A1 (en) * | 1995-12-22 | 1997-06-26 | Bayer Ag | Process for the preparation of 2-chloro-5-chloromethylthiazole |
-
1978
- 1978-02-14 JP JP1612778A patent/JPS54109969A/en active Granted
-
1979
- 1979-01-26 CA CA000320315A patent/CA1116609A/en not_active Expired
- 1979-02-13 ES ES477646A patent/ES477646A1/en not_active Expired
- 1979-02-13 SE SE7901250A patent/SE437987B/en not_active IP Right Cessation
- 1979-02-13 IT IT20146/79A patent/IT1113001B/en active
- 1979-02-13 DK DK60979A patent/DK60979A/en not_active Application Discontinuation
- 1979-02-14 CH CH142679A patent/CH639963A5/en not_active IP Right Cessation
- 1979-02-14 AR AR275509A patent/AR221715A1/en active
- 1979-02-14 ZA ZA79673A patent/ZA79673B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| IT7920146A0 (en) | 1979-02-13 |
| CH639963A5 (en) | 1983-12-15 |
| JPS54109969A (en) | 1979-08-29 |
| JPS6229432B2 (en) | 1987-06-25 |
| CA1116609A (en) | 1982-01-19 |
| SE7901250L (en) | 1979-08-15 |
| IT1113001B (en) | 1986-01-20 |
| DK60979A (en) | 1979-08-15 |
| AR221715A1 (en) | 1981-03-13 |
| ZA79673B (en) | 1980-05-28 |
| SE437987B (en) | 1985-03-25 |
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