Methyl iodide → HCID 67529325, compound

HRID 602574Notes

Reaction equation

HRID 602574 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][C:3]=1[N:12]1[C:16]([CH3:17])=[CH:15][S:14][C:13]1=[S:18].[CH3:19][I:20]>CC(C)=O>[I-:20].[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:9])([F:10])[F:11])=[CH:4][C:3]=1[N+:12]1[C:16]([CH3:17])=[CH:15][S:14][C:13]=1[S:18][CH3:19]

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 59324090HCID 59324090, compound

Product 1

HCID 67529325HCID 67529325, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

1.34 g (4.61 mmol) of 3-[2-amino-5-(trifluoromethyl)phenyl]-4-methyl-1,3-thiazole-2(3H)-thione were solubilised in acetone (25 mL), then CH3I (10 eq, 2.87 mL) was added and the solution stirred at r.t. for 12 h. 3-[2-amino-5-(trifluoromethyl)phenyl]-4-methyl-2-(methylsulfanyl)-1,3-thiazol-3-ium iodide (3a) was recovered by filtration (white powder, 1.19 g, 60%) and by evaporation of the organic layer (776 mg, 39%). Mp 194° C.; 1H NMR (300 MHz, CD3OD) δ=2.27 (3H, d, J=1.1, CH3), 2.96 (3H, s, SCH3), 7.10-7.18 (1H, m, Ar), 7.62-7.70 (2H, m, Ar), 7.86 (1H, q, J=1.1, H5); 13C NMR (75 MHz, CD3OD) δ=13.74, 18.11, 118.28, 118.36, 118.68, 119.97 (q, J=34), 125.41 (q, J=270), 126.91 (q, J=4), 130.92 (q, J=4), 149.97, 148.73, 182.40; HRMS m/z C12H12N2F3S2 [M−I]+ calcd: 305.0388, found: 305.0389.

Workup

  1. filtration3-[2-amino-5-(trifluoromethyl)phenyl]-4-methyl-2-(methylsulfanyl)-1,3-thiazol-3-ium iodide (3a) was recovered by filtration (white powder, 1.19 g, 60%) and by evaporation of the organic layer (776 mg, 39%)

Sources & evidence

ORD record
ord-349e57088cb249dbaae0bc718ee7d14b
Source dataset
uspto-grants-2011_03
Patent number
US07906541B2

Reaction notes

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