Methyl iodide → (NZ)-3-methyl-N-[5-methyl-3-[4-(trifluoromethyl)phenyl]-1,3-thiazol-2-ylidene]imidazol-3-ium-1-carboxamide;iodide

HRID 390696Notes

Reaction equation

HRID 390696 reaction equation
[CH3:1][C:2]1[S:6]/[C:5](=[N:7]\[C:8]([N:10]2[CH:14]=[CH:13][N:12]=[CH:11]2)=[O:9])/[N:4]([C:15]2[CH:20]=[CH:19][C:18]([C:21]([F:24])([F:23])[F:22])=[CH:17][CH:16]=2)[CH:3]=1.[I:25][CH3:26]>C(#N)C>[I-:25].[CH3:26][N+:12]1[CH:13]=[CH:14][N:10]([C:8](/[N:7]=[C:5]2\[S:6][C:2]([CH3:1])=[CH:3][N:4]\2[C:15]2[CH:16]=[CH:17][C:18]([C:21]([F:24])([F:22])[F:23])=[CH:19][CH:20]=2)=[O:9])[CH:11]=1

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 87450752(NZ)-N-[5-methyl-3-[4-(trifluoromethyl)phenyl]-1,3-thiazol-2-ylidene]imidazole-1-carboxamide

Product 1

HCID 87447393(NZ)-3-methyl-N-[5-methyl-3-[4-(trifluoromethyl)phenyl]-1,3-thiazol-2-ylidene]imidazol-3-ium-1-carboxamide;iodide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

N-[(2Z)-5-methyl-3-[4-(trifluoromethyl)phenyl]-1,3-thiazol-2(3H)-ylidene]-1H-imidazole-1-carboxamide (2.0 g, 5.68 mmol, Example 18A) in acetonitrile (10 mL) was treated with iodomethane (3 mL). The mixture was stirred at room temperature for five days, the solvent was evaporated, and the title product was used directly for the next step.

Workup

  1. customthe solvent was evaporated

Sources & evidence

ORD record
ord-c97093caa2754b079764acbc5cafc707
Source dataset
uspto-grants-2013_02
Patent number
US08383657B2

Reaction notes

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