Benzothiazole 2-methylthio

Brownlee BG, JH Carey, GA Macinnes, IT Pellizzari (1992) Aquatic environmental chemistry of 2-(thiocyano-methylthio)benzothiazole and related benzothiazoles. Environ Toxicol Chem 11 1153-1168. 

In soft cheeses, such as Brie, Camembert, and Limburger, the following sulfur compounds were implicated 3-(methylthio)propanol, MT, DMS, DMDS, DMTS, dimethyl tetrasulfide, methyl ethyl disulfide, diethyl disulfide, 2,4-dithiapentane, 3-methylthio-2,4-dithiapentane, methional, 2,4,5-trithiahex-ane, 1,1-fe-methylmercaptodisulfide, methyl thioacetate (=methanethiol acetate), benzothiazole, methylthiobenzothiazole, methyl ethyl sulfonate, methyl methane thiosulfonate, thiophene 2-aldehyde, and H2S.34 Many of these were only present in small amounts Limburger cheese was notable for 13.2% of DMDS, 0.5% of methyl thioacetate, and 0.8% of DMTS. 

Diethyl benzothiazol-2-ylidenemalonate (1675) was prepared in the reaction of diethyl bis(methylthio)methylenemalonate and 2-aminothiophenol in boiling ethanol for 16 hr in 78% yield (90CB541). 

A convenient synthesis of l//-indolyl-2-benzothiazoles in moderate yield by the direct conversion of indole-2- and 5-carboxylates with in situ generated trimethylaluminum-2-aminothiophenol was described. [95H1045] 2-Substituted 1,3-benzothiazoles having a variety of substituents can be prepared from 2-methylthio-N-triphenylphosphoranylideneaniline and acid chlorides by iminophosphorane-mediated cyclization. [95H455]... 

The first group of sulphur compounds mentioned above can be defined as common fermentative sulphur volatiles (CFSV) and includes in our presentation ethylmercaptan (EtSH), dimethyl sulphide (DMS), diethyl sulphide (DES), dimethyl disulphide (DMDS), diethyl disulphide (DEDS), methyl thioacetate (MTA), ethyl thioacetate (ETA), 2-mercaptoethanol (ME), 2-(methylthio)-l-ethanol (MTE), 3-(methylthio)-l-propanol (MTP), 4-(methylthio)-l-butanol (MTB), benzothiazole (BT) and 5-(2-hydroxyethyl)-4-methylthiazole (HMT) (see Table 5.6). 

Figure 5.2. Volatile sulfur compounds of wines (15) dimethyl sulfide, (16) ethylmer-captan, (17) diethyl sulfide, (18) methyl thioacetate, (19) dimethyl disulfide, (20) ethyl thioacetate, (21) diethyl disulfide, (22) 2-mercaptoethanol, (23) 2-(methylthio)-l-ethanol, (24) 3-(methylthio)-l-propanol, (25) 4-(methylthio)-l-butanol, (26) 3-mercap-tohexan-l-ol, (27) 4-methyl-4-mercaptopentan-2-one, (28) 3-mercaptohexanol acetate, (29) benzothiazole, (30) 5-(2-hydroxyethyl)-4-methylthiazole, (31) fra s-2-methylthio-phan-3-ol, (32) 2-methyltetrahydrothiophen-3-one.

Durch Pyrolyse von pDiphenyl-ethenyl)- (I Schmp. 108°) und 22% 2-(l,2-Diphenyl-ethyl)-l,3-benzothiazol (III). Das 1,3-Benzothiazol I muB vor Tageslicht geschiitzt werden, da sonst Isomerisierung zur tra/w-Verbindung II stattfindet328 ... 

Methylthio-l,3-benzothiazol laBt sich mit Dimethylsulfat und Diethylsulfat alkylieren z.B.365 ... 

Methylthio- und 2-Dimethylamino-l,3-benzothiazol lassen sich mit 0-(2,4,6-Trimethyl-benzolsulfonyl)-hydroxylamin N-aminieren401 ... 

Die Reaktion von 2-Methylthio-l,3-benzothiazol liefert 2-Methylthio-6-sulfo-l,3-benzothia-zo/435. 

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