Title:
PROCESS FORPREPARATION OF ALKOXYBENZAMIDES AND THIAZOLYL ISOCYANATES
Document Type and Number:
WIPO Patent Application WO/2003/078412
Kind Code:
A1
Abstract:
Alkoxybenzamides represented by the general formula (3): (3) [wherein R1 to R5 are each H, alkyl, or alkoxy; R6 is an aromatic heterocyle; and A is O or S] are produced by reacting an alkoxybenzene represented by the general formula (1): (1) with an isocyanate represented by the general formula (2): (2) in the presence of a Lewis acid. Further, thiazolyl isocyanates of the general formula (5) included among the isocyanates of the general formula (2) are prepared from aminothiazoles and carbonyl halides: (5) [wherein R1 is H, alkyl, alkoxy, or the like; and R2 is H, halogeno, alkyl, or the like, with the proviso that the cases wherein both R1 and R2 are H are excepted]. The invention enables production of alkoxybenzamides in fewer steps in high yield and also provides thiazolyl isocyanates useful for the production of ureas, carbamates, and aromatic amides bearing thiazole rings.
Inventors:
AWANO HIROKAZU (JP)
KOITO MITSUO (JP)
KUSUMOTO MASAHIKO (JP)
KOITO MITSUO (JP)
KUSUMOTO MASAHIKO (JP)
Application Number:
PCT/JP2003/003211
Publication Date:
September 25, 2003
Filing Date:
March 18, 2003
Export Citation:
Assignee:
MITSUI CHEMICALS INC (JP)
AWANO HIROKAZU (JP)
KOITO MITSUO (JP)
KUSUMOTO MASAHIKO (JP)
AWANO HIROKAZU (JP)
KOITO MITSUO (JP)
KUSUMOTO MASAHIKO (JP)
International Classes:
C07D277/38; C07D277/46; (IPC1-7): C07D277/46
Foreign References:
| EP0994108A1 | 2000-04-19 | |||
| US4097485A | 1978-06-27 | |||
| US4086240A | 1978-04-25 | |||
| US4116969A | 1978-09-26 |
Other References:
BRADBURY B.J.: "Synthesis of 4,7-disubstituted spirobenzofuran-2 (3H)-cyclohexanes", JOURNAL OF HETEROCYCLIC CHEMISTRY, vol. 26, no. 6, 1989, pages 1827 - 1833, XP002968805
ROSS K.T.: "Synthesis of cervinomycins A1 and A2", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 111, no. 12, 1989, pages 4522 - 4524, XP002968806
LIANG C.D.: "Regioselective aromatic ring functionalization of dopamine analogs", TETRAHEDRON LETTERS, vol. 27, no. 18, 1986, pages 1971 - 1974, XP002968807
HONDA I.: "Synthesis of 3-nitro-2,4,6-trihydroxybenzamide and thiobenzamide derivatives as highly potent inhibitors of photosynthetic electron transport", AGRICULTURAL AND BIOLOGICAL CHEMISTRY, vol. 54, no. 4, 1990, pages 1071 - 1072, XP002968808
See also references of EP 1489073A4
ROSS K.T.: "Synthesis of cervinomycins A1 and A2", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 111, no. 12, 1989, pages 4522 - 4524, XP002968806
LIANG C.D.: "Regioselective aromatic ring functionalization of dopamine analogs", TETRAHEDRON LETTERS, vol. 27, no. 18, 1986, pages 1971 - 1974, XP002968807
HONDA I.: "Synthesis of 3-nitro-2,4,6-trihydroxybenzamide and thiobenzamide derivatives as highly potent inhibitors of photosynthetic electron transport", AGRICULTURAL AND BIOLOGICAL CHEMISTRY, vol. 54, no. 4, 1990, pages 1071 - 1072, XP002968808
See also references of EP 1489073A4
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