2- Mercapto-l-methylimidazole

The l-acyl-3-methylimidazole-2-thiones are easily obtained either from bis-l-methyl-2-imidazole disulfide, a carboxylic acid, and triphenylphosphine, or from 2-mercapto-l-methylimidazole and a carboxylic acid chloride in the presence of triethylamine.[32 ... 

Thus, 5-amino-2-mercapto-l-methylimidazole (96 R = Me, R2 = SH) (65%) was obtained (48JCS2028) from 5-amino-2-methylaminothiazole (113 R1 = Me) on treatment with aqueous sodium carbonate. The aminoim-idazole (96 R1 = Me, R2 = SH) was found to be unstable in air, but gave a stable hydrochloride salt and on treatment with Raney nickel was desulfurized to give 5-amino-1-methylimidazole (96 R = Me, R2 = H) (58%), which was also unstable in air and was characterized as its picrate salt. 

Mononuclear complex formation was confirmed for the adduct of zinc(II) salt with 2-mercaptobenzothiazole and o-phenanthroline (253). The t/-S coordination is observed in the complexes of triphenylphos-phine gold with 2-mercapto-l-methylimidazole (254) (88JOM119), 8-mercaptotheophilline (255) (91IC3743), 2-mercaptobenzoxazole (256) [94AX(C)1420], and purine-6-thiol (257) (94AJC577). 

MERCAPTO-l-METHYLIMIDAZOLE see MC0500 N-(MERCAPTOMETHYL)PHTHAIJMIDE S-(0,0-DIMETHYL PHOSPHORODITHIOATE) see PHX250 2-MERCAPTO-6-METHYLPYRIMID-4-ONE see MPW500... 

Reaction of 2-mercapto-l-methylimidazole and 2-mercapto-l-mesitylimidazole with LiBH4 in toluene produces the corresponding lithiated derivatives. The bidentate coordination of the sulfur atoms to lithium is augmented by donation from one of the B—H groups of the imidazole ligands. In the mesityl derivative, Li—B = 2.80, 3.09 A (values for two independent molecules) ... 

The preparation of complexes of Pd, Pt, and Rh with some N- and S-containing heterocycles has been reported. The complexes isolated, cis- and trans-[ML2X2] [M = Pd or Pt L = 2-mercaptothiazoline (SHTH), 2-mercaptobenzothiazole (SHBTZ), and 2-mercapto-l-methylimidazole (SHMI) X = Cl or I] and [ML2] (M = Pd or Pt L = SHBTZ or SHMI), were shown to possess only N-bonded L in acidic media, whereas in basic solution SHTH bonds only through S, and SHBTZ and SHMI are S,N-chelated. 

Fig. 3 Double-stranded chain structure in the halogen-bonded co-crystal 5 between 2-mercapto-l-methylimidazole (1) and 1,4-diiodotetrafluorobenzene (2). Halogen-bonding distances S-. 1=3.314(1) A. 3.342(1) A. Colors are as follows black 70%—nitrogen black 50%—iodine black 30%—fluorine and hydrogen black 10%—sulfur and carbon. Dashed lines represent intermolecular halogen and hydrogen bondings. (View this art in color at www.dekker.com)...

The reaction of [N3P3CI6] with appropriate amounts the sodium salts of 2-mercapto-l-methylimidazole gave the new mono or multi-geminally substituted cyclophosphazenes with thiolate groups (117) and (118), while the reaction with... 

Raby, C., Claude, J., Moesch, C. and Buxeraud, J. (1979) Charge-transfer complexing between 2-mercapto-l-methylimidazole and iodine. C. R. Acad. ScL, Ser. IIC, 288, 319-322. 

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