The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Synthesis of thiazole derivatives. XVII. Hydroxymethyl- substituted 2-methylthiazoles》. Authors are Zubarovskii, V. M.; Moskaleva, R. N..The article about the compound:(2-Methylthiazol-4-yl)methanolcas:76632-23-0,SMILESS:OCC1=CSC(C)=N1).Quality Control of (2-Methylthiazol-4-yl)methanol. Through the article, more information about this compound (cas:76632-23-0) is conveyed.
cf. CA 55,514b; 56, 15495i. Et 2-methylthiazole-4-carboxylate and LiAlH4, in Et2O gave 66-9% 2-methyl-4-(hydroxymethyl)thiazole (I), b5 104°, which solidified on cooling; methiodide m. 208°; Me p-totuenesulfonate (from Ag p-toluenesulfonate and the methiodide) m. 128°; Et p-toluenesulfonate, m.p. unstated. Similarly was prepared 63-5% 2-methyl-5-(hydroxymethyl)thiazole (II), b3 117.5°; methiodide m. 186°; ethiodide m. 136-7°. I and Ac2O refluxed 4 hrs. gave I acetate, b10 111°; II acetate b7 104°. I and PCl5 in MePh 15 min. at 110° gave, after an aqueous treatment and neutralization, 63.2% 2-methyl-4-(chloromethyl)thiazole, b10 84°, a mild eye irritant. Similarly was prepared 2-methyl-5-(chloromethyl)thiazole, b13 93.5° (91%). The chloromethyl derivatives and EtONa in EtOH gave: 2-methyl-4-(ethoxymethyl)thiazole, b13 93.5° (Et p-toluenesulfonate, 94%, undescribed); 2-methyl-5-(ethoxymethyl)thiazole, 65.5%, b7 73° (Et p-toluenesulfonate, 85%, undescribed). Condensation of these thiazoles with the usual components of cyanine dye intermediates (p-Me2NC6H4CHO, 2-(methylthio)benzothiazole Et tosylate, HC(OEt)3, 2-(anilinovinyl)-5-methoxybenzothiazole Et tosylate, and 2-(acetanilidovinyl)benzothiazole Et tosylate) gave the following dyes: [3-methyl-5-(hydroxymethyl)-2-thiazole](3-ethyl-2-benzothiazole)cyanine iodide, 21%, decompose 256°, λmaximum 414 mμ; [3-methyl-5-(hydroxymethyl)-2-thiazole](3-ethyl-2- benzothiazole)cyanine iodide, 16%, decompose 296°, λmaximum 417 mμ; 3,3′-diethyl-4,4′-bis(hydroxymethyl)thiazolocarbocyanine perchlorate, 12%, decompose 183°, λmaximum 553 mμ; 3,3′-diethyl-5,5′-bis(hydroxymethyl)thiazolocarbocyanine perchlorate, 13%, decompose 191°, λmaximum 555 mμ; [3-methyl-4-(hydroxymethyl)-2-thiazole] (3-ethyl-5-methoxy-2-benzothiazole)trimethinecyanine perchlorate, 87%, m. 167°, λmaximum 560 mμ; [3-methyl-5-(hydroxymethyl)-2-thiazole] [3-ethyl-5-(methoxymethyl)-2-benzothiazole]-trimethinecyanine perchlorate, 85%, m. 176°, λmaximum 567 mμ; [3-methyl-4-(hydroxymethyl)-2-thiazole] (3-ethyl-4,5-benzo-2-benzothiazole)trimethinecyanine perchlorate, 52%, decompose 236°, λmaximum 568 mμ; [3-methyl-5-(hydroxymethyl)-2-thiazole] (3-ethyl-4,5-benzo-2-benzothiazole)trimethinecyanine perchlorate, 42%, decompose 241°, λmaximum 571 mμ; 2-(p-dimethylaminostyryl)-4-(hydroxymethyl)thiazole Me tosylate, 54%, decompose 297°, λmaximum 485 mμ; 2-(p-dimethylaminostyryl)-4-(ethoxymethyl)thiazole Et perchlorate, 60%, m. 168°, λmaximum 491 mμ; 2-(p-dimethylaminostyryl)-4-(acetoxymethyl)thiazole Et perchlorate, 40%, m. 193°, λmaximum 496 mμ; 2-(p-dimethylaminostyryl)-5-(hydroxymethyl)thiazole Me tosylate, 90%, m. 212°, λmaximum 489 mμ; 2-(p-dimethylaminostyryl)-5-(ethoxymethyl)thiazole Et perchlorate, 18%, m. 167°, λmaximum 492 mμ; and 2-(p-dimethylaminostyryl)-5-(acetoxymethyl)thiazole Et perchlorate, 42%, m. 195° λmaximum 500 mμ.
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Reference:
Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem