4-Methyl-5-thiazole Ethanol

Methyl Propyl 3-Methyl Butyrate, 84 4-Methyl-5-thiazole Ethanol, 84 Nerolidol, 84... 

A Anisole 21A 2-Hexenyl acetate 38A 4-Methyl-5-thiazole ethanol... 

Schatzmann, in 1891, tried to prepare 2-thiazolines by hydrogenation of thiazoles and by the action of sodium and ethanol on 2,4-dimethyl-thiazole, 2-methylthiazole, and 2-methyl-4-phenylthiazole (476). None of these substrates was reduced to thiazoline the second gave no reaction and the first underwent ring cleavage, leading to a mixture of n-propylmercaptan and ethylamine (Scheme 90). Three years later the same... 

Alkylation of 5-phenylrhodanines (122) with alkyl iodides and sodium ethoxide yields the meso-ionic 2-alkylthio-l,3-thiazol-4-ones (114, R = SR) 78a structure of the compound 114, R = SMe, R = NHj, R = Ph, was established by X-ray analysis. The dipole moment of the compound 114, R = R = Me, R = Ph, in benzene solution is 5.21 D. Irradiation of the meso-ionic l,3-thiazole-4-thione (114, R = SMe, R = Me, R = Ph) in ethanol yields the isomeric 3-methyl-4-methylthio-5-phenyl-l,3-thiazol-2-one. A novel mechanism for this photochemical rearrangement has been proposed. ... 

The compound 3-(2-Bromoacetyl)-4-hydroxychromen-2-one (18) reacts with thiourea to afford 3-(2-amino-thiazol-4-yl)-4-hydroxychromen-2-one hydrobromide (19a). This reaction was carried out in boiling ethanol for 30 min. Compound 19a also gave positive coloration with iron(III) chloride solution (Scheme 7). In the reaction of compound 18 with 1-methylthiourea under identical experimental conditions as above, 4-hydroxy-3-(2-methyl-aminothiazol-4-yl)chromen-2-one (19b) in 67% yield was obtained. In a similar manner, 18 reacted with three arylthiourea derivatives affording the corresponding 3-(2-arylthiazol-4-yl)chromen-2-ones (19c-e) in different yields (70, 63 and 74%, respectively). The derivatives formed in these reactions were identified as 4-hydroxy-3-(2-phenylaminothiazol-4-yl)chromen-2-one(19c), 4-hydroxy-3-(2-p-tolylaminothiazol-4-yl)chromen-2-one (19d) and 4-hydroxy-3-2-(4-methoxyphenylamino)thiazol-4-yl)chromen-2-one (19e). The identities of these compounds were established by spectral data and elemental analysis. 

As in the case of pyridine, the quaternization of thiazole induces a bathochromic shift of the UV absorption spectrum. In ethanol the long wavelength maximum at 233 nm (log e = 3.59) for thiazole moves to 240 nm (log s = 3.62) for 3-methylthiazolium tosylate. As in the case of the free bases, the substitution of a nuclear hydrogen atom by a methyl group induces a bathochromic shift that decreases in the order of the position substituted, 4- > 5- > 2-, and this perturbation could be accounted for by a theoretical model based on the PPP 7r method, using the fractional core charge approximation (72BSF3862). 

Br Ethanol Ruckfl. 1 2-Methyl-8H-(Jndeno[l, 2-d -l, 3-thiazol y-Hydrobromid 21 (Schmp. 266-267,5r) 1083... 

Amino-4-(methoxycarbonyl-methyl)-l,3-thiazol (R1 = CH2-COOCH,)947 Eine Suspension von 2,0 g (25 mmol)Thioharnstolf in 75 ml Ethanol wird mit 3,75 g (25 mmol) 4-Chlor-3-oxo-butansaure-methylester versetzt und 4 h unter Rfihren unter RuckfluB erhitzt. Dabei scheidet sich allmahlich das farblosc Hydrochlorid des Endproduktes ab. Nach dem Abkfihlen wird abgesaugt, mit etwas Ethanol gewaschen, getrocknet und aus 2-Propanol umkristallisiert Ausbeute (Hydrochlorid) 4,3 g (83%) Schmp. 174°. 

N- -CH3 c6hs Br Ethanol Riickfl. 1 2-( 4-Methyl-l, 3-thiazol-2-ylamino )- 90 245 353... 

Amino-5-(2-hydroxy-ethyl)-4-methyl-l,3-thiazol-Hydrochlorid (R1 = CH3 R2 = CH2—CH2—OH)159 Eine Mischung von 45,6 g (0,6 mol) Thioharnstoff und 81,6 g (0.6 mol) 3-Chlor-5-hydroxy-2-oxo-pentan in 600 ml Wasser wird unter RuckfluB erhitzt. Nach dem Abkiihlen wird die Losung mit Diethylether ge-waschen. Man dampft die waBr. Phase ein. Der Riickstand wird i. Vak. (5 Torr/0,67 kPa) bei 60° getrocknet und aus Aceton/Ethanol umkristallisiert Ausbeute 73 g (77%) Schmp. 156-157°. 

CO-NH-C6H5 ch3 Cl Cl Ethanol Ruckfl. 10 2- ( Anilinocarbony lamina )-5-chlor-4-methyl-l, 3-thiazol 56 222 337... 

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