Methyl iodide → HCID 67529941, compound

HRID 602580Notes

Reaction equation

HRID 602580 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[N:9]1[C:13]([CH3:14])=[CH:12][S:11][C:10]1=[S:15].[CH3:16][I:17]>CC(C)=O>[I-:17].[NH2:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[N+:9]1[C:13]([CH3:14])=[CH:12][S:11][C:10]=1[S:15][CH3:16]

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 59324083HCID 59324083, compound

Product 1

HCID 67529941HCID 67529941, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

3 g (12.5 mmol) of 3-(2-amino-4-fluorophenyl)-4-methyl-1,3-thiazole-2(3H)-thione 2b obtained in stage A were solubilised in acetone (100 mL), then CH3I (10 eq, 7.8 mL) was added and the solution stirred at r.t. for 12 h. 3-(2-Amino-4-fluorophenyl)-4-methyl-2-(methylsulfanyl)-1,3-thiazol-3-ium iodide (3b) was recovered by filtration (pale yellow powder, 4.7 g, 98%). Mp=206° C.; 1H NMR (300 MHz, CD3OD) δ=2.26 (3H, d, J=1.1, CH3), 2.94 (3H, s, SCH3), 6.51-7.27 (3H, m, Ar), 7.82 (1H, q, J=1.1, H5); 13C NMR (75 MHz, CD3OD) δ=13.79, 17.97, 104.17 (d, J=27), 105.83 (d, J=25), 115.66 (d, J=2), 117.98, 130.83 (d, J=12), 147.65 (d, J=1), 148.28, 166.95 (d, J=248), 182.41; HRMS m/z C11H12N2FS2 [M−I]+ calcd: 255.0420, found: 255.0417.

Workup

  1. filtration3-(2-Amino-4-fluorophenyl)-4-methyl-2-(methylsulfanyl)-1,3-thiazol-3-ium iodide (3b) was recovered by filtration (pale yellow powder, 4.7 g, 98%)

Sources & evidence

ORD record
ord-7c754b53a64040389c1a12d1b19cb3f2
Source dataset
uspto-grants-2011_03
Patent number
US07906541B2

Reaction notes

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