Methyl iodide → N-(1-(methylthio)ethylidene)-2,4-dichlorobenzamide

HRID 1794992Notes

Reaction equation

HRID 1794992 reaction equation
[C:1]([NH:4][C:5](=[O:14])[C:6]1[CH:11]=[CH:10][C:9]([Cl:12])=[CH:8][C:7]=1[Cl:13])(=[S:3])[CH3:2].[C:15]([O-])([O-])=O.[K+].[K+].IC>C(#N)C>[CH3:15][S:3][C:1](=[N:4][C:5](=[O:14])[C:6]1[CH:11]=[CH:10][C:9]([Cl:12])=[CH:8][C:7]=1[Cl:13])[CH3:2]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 22184681HCID 22184681, compound

Product 1

HCID 22184679N-(1-(methylthio)ethylidene)-2,4-dichlorobenzamideYield 96.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of N-(thioacetyl)-2,4-dichlorobenzamide (400 mg, 1.6 mmol) and K2CO3 (445 mg, 3.22 mmol) in anhydrous acetonitrile (20 mL) was stirred at ambient temperature. Iodomethane (458 mg, 0.2 mL, 3.22 mmol) was added and the reaction mixture was then stirred for 2.5 h. Solvent was removed in vacuo and the residue was partitioned between ether and water. The combined organic layers were dried over MgSO4, filtered and concentrated in vacuo to give an oil (406 mg): NMR (CDCl3, 300 MHz): δ 7.86 (d, 1H, J=8), 7.47 (d, 1H, J=2), 7.32 (dd, 1H, J=8, 2), 2.40 (s, 3H), 2.29 (s, 3H).

Workup

  1. stirringthe reaction mixture was then stirred for 2.5 h
  2. customSolvent was removed in vacuo
  3. customthe residue was partitioned between ether and water
  4. dry with materialThe combined organic layers were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c963dd99338f4f79b2e98779cb4691cc
Source dataset
uspto-grants-2006_04
Patent number
US07026317B2

Reaction notes

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