Methyl iodide → HCID 12754790, compound

HRID 2220869Notes

Reaction equation

HRID 2220869 reaction equation
[C:1](=[S:3])=[S:2].[NH2:4][C:5]1[CH:6]=[C:7]([C:11]([F:14])([F:13])[F:12])[CH:8]=[CH:9][CH:10]=1.[OH-].[Na+].[CH3:17]I>CS(C)=O.O>[CH3:17][S:2][C:1](=[S:3])[NH:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([C:11]([F:12])([F:13])[F:14])[CH:6]=1

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 6348Carbon DisulfideHCID 73753-(Trifluoromethyl)anilineHCID 14798Sodium Hydroxide

Product 1

HCID 12754790HCID 12754790, compoundYield 71%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

Under an atmosphere of nitrogen, carbon disulfide (0.73 ml, 12 mmol) was added to a solution of 3-aminobenzotrifluoride (1.50 g, 9.3 mmol) in DMSO (10 ml). Subsequently, sodium hydroxide (0.56 ml, solution in water, 20 mol/l, 11 mmol) was added, and the dark brown reaction mixture was stirred for 30 min (r.t.). Upon the addition of methyl iodide (730 ml, 12 mmol), the mixture turned yellow and was stirred overnight (r.t.). The reaction mixture was poured into water and extracted with ethyl acetate. The extract was dried (Na2SO4), and the solvent evaporated under reduced pressure. The title compound (1.65 g, 71%) was obtained by purification of the residue (silica gel, heptan/ethyl acetate=100:0-80:20).

Workup

  1. stirringwas stirred overnight (r.t.)
  2. extractionextracted with ethyl acetate
  3. dry with materialThe extract was dried (Na2SO4)
  4. customthe solvent evaporated under reduced pressure

Sources & evidence

ORD record
ord-e8913e70fb5245b096012c1ca0342260
Source dataset
uspto-grants-2008_05
Patent number
US07368454B2

Reaction notes

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