Methyl iodide → HCID 59529734, compound

HRID 1952344Notes

Reaction equation

HRID 1952344 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([O:10][C:11]2[C:16]([Cl:17])=[C:15]([CH3:18])[NH:14][C:13](=[O:19])[C:12]=2[Cl:20])[CH:9]=1)[C:5]#[N:6].[CH3:21]I>C(=O)([O-])[O-].[Ag+2].C(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([O:10][C:11]2[C:16]([Cl:17])=[C:15]([CH3:18])[N:14]=[C:13]([O:19][CH3:21])[C:12]=2[Cl:20])[CH:9]=1)[C:5]#[N:6]

Participants

5

Reactant 2

HCID 6328Methyl iodideHCID 59529763HCID 59529763, compound

Product 1

HCID 59529734HCID 59529734, compound

Reagents, catalysts & solvents 2

HCID 178418647HCID 178418647, compoundCatalystHCID 6212ChloroformSolvent

Conditions

Temperature
50 °C

Procedure

Compound 5-1 (3.2 g; 9.71 mmol), methyl iodide (1.21 mL; 19.4 mmol), silver carbonate (8.03 g; 29.1) mmol) and chloroform (100 mL) were added to a sealed vessel. The contents of the sealed vessel were heated at 50° C. overnight in the absence of light. The reaction mixture was cooled to room temperature, filtered to remove insoluble material, and the filtrate concentrated in vacuo. The crude material was purified via silica gel chromatography (0-15% EtOAc in hexane) to give the title compound. MS M+1=344.8. 1H NMR (CDCl3): 2.58 (s, 3H), 4.06 (s, 3H), 6.96 (m, 1H), 7.20 (m, 1H), 7.38 (m, 1H).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationfiltered
  3. customto remove insoluble material
  4. concentrationthe filtrate concentrated in vacuo
  5. customThe crude material was purified via silica gel chromatography (0-15% EtOAc in hexane)

Sources & evidence

ORD record
ord-5554e0bc83fc415286eacd1e03c1daa4
Source dataset
uspto-grants-2013_03
Patent number
US08404856B2

Reaction notes

Loading…