Methyl iodide → HCID 178423597, compound

HRID 2220868Notes

Reaction equation

HRID 2220868 reaction equation
CI.[NH2:3][C:4]1[CH:24]=[CH:23][CH:22]=[C:21]([CH3:25])[C:5]=1[CH2:6][NH:7][C:8]([NH:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([C:17]([F:20])([F:19])[F:18])[CH:12]=1)=S>C(O)C>[CH3:25][C:21]1[CH:22]=[CH:23][CH:24]=[C:4]2[C:5]=1[CH2:6][NH:7][C:8]([NH:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([C:17]([F:20])([F:19])[F:18])[CH:12]=1)=[N:3]2

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 86607791HCID 86607791, compound

Product 1

HCID 178423597HCID 178423597, compoundYield 8.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of methyl iodide (167 mg, 1.18 mmol) and 1-(2-amino-6-methyl-benzyl)-3-(3-trifluoromethyl-phenyl)-thiourea (50 mg, 0.147 mmol) in ethanol (3 ml) was heated to reflux for 3 h. The solvent was evaporated under reduced pressure, the residue was taken up in ethyl acetate, washed (water), and dried (Na2SO4). After evaporation of the solvent under reduced pressure, the title compound (4 mg, 8.9%, MS: m/e=306.1 [M+H+]) was obtained by HPLC purification of the residue (YMC CombiPrep C18 column 50×20 mm, solvent gradient 5-95% CH3CN in 0.1% TFA(aq) over 6.0 min, λ=230 nm, flow rate 40 ml/min).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 3 h
  3. customThe solvent was evaporated under reduced pressure
  4. washwashed (water)
  5. dry with materialdried (Na2SO4)
  6. customAfter evaporation of the solvent under reduced pressure

Sources & evidence

ORD record
ord-92dd3340c9d844dd8f7173834459058a
Source dataset
uspto-grants-2008_05
Patent number
US07368454B2

Reaction notes

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