Methyl iodide → HCID 86641708, compound

HRID 602577Notes

Reaction equation

HRID 602577 reaction equation
[CH3:1][C:2]1[N:9]2[C:5](=[N:6][C:7]3[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][C:8]=32)[S:4][CH:3]=1.[CH3:18][I:19]>CC(C)=O>[I-:19].[CH3:1][C:2]1[N:9]2[C:5](=[N+:6]([CH3:18])[C:7]3[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:15])[F:16])=[CH:10][C:8]=32)[S:4][CH:3]=1

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 59324084HCID 59324084, compound

Product 1

HCID 86641708HCID 86641708, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

375 mg (1.46 mmol) of 3-methyl-6-(trifluoromethyl)[1,3]thiazolo[3,2-a]benzimidazole 5a were solubilised in acetone (15 mL), then CH3I (10 eq, 0.9 mL) was added and the solution stirred at r.t. for 12 h. 3,9-dimethyl-6-(trifluoromethyl)[1,3]thiazolo[3,2-a][3,1]benzimidazol-9-ium iodide 6a was recovered by evaporation of the solvent (orange powder, 570 mg, 98%). Mp=>270° C.; 1H NMR (300 MHz, DMSO-d6) δ=2.94 (3H, d, J=1.2, CH3), 4.18 (3H, s, NH3), 7.51 (1H, q, J=1.2, H5), 8.13-8.17 (1H, m, Ar), 8.28-8.21 (1H, m, Ar), 8.52-8.56 (1H, m, Ar); 13C NMR (75 MHz, DMSO-d6) δ=13.44, 33.35, 111.68 (q, J=4), 112.76, 113.98, 123.59 (q, J=4), 123.95 (q, J=272), 124.08 (q, J=33), 126.48, 133.42, 138.76, 157.50; HRMS m/z C12H10F3N2S [M−I]+ calcd: 271.0511, found: 271.0513.

Workup

  1. custom3,9-dimethyl-6-(trifluoromethyl)[1,3]thiazolo[3,2-a][3,1]benzimidazol-9-ium iodide 6a was recovered by evaporation of the solvent (orange powder, 570 mg, 98%)

Sources & evidence

ORD record
ord-9e9608ab214345cb9d11db40c9307f8c
Source dataset
uspto-grants-2011_03
Patent number
US07906541B2

Reaction notes

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