Methyl iodide → HCID 21930404, compound

HRID 1178458Notes

Reaction equation

HRID 1178458 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([O:10][C:11]2[CH:16]=[C:15]([OH:17])[CH:14]=[C:13]([CH:18]=[O:19])[CH:12]=2)[CH:3]=1.[H-].[Na+].[CH3:22]I>CN(C=O)C.O>[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([O:10][C:11]2[CH:16]=[C:15]([O:17][CH3:22])[CH:14]=[C:13]([CH:18]=[O:19])[CH:12]=2)[CH:3]=1

Participants

6

Reactant 3

HCID 6328Methyl iodide2×HCID 24758Sodium hydride2×HCID 21930398HCID 21930398, compound

Product 1

HCID 21930404HCID 21930404, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

4-Chloro-2-(3-formyl-5-hydroxyphenoxy)benzonitrile (0.20 g, 0.75 mmol) in DMF (5 ml) was treated with sodium hydride (60% in mineral oil, 30 mg, 0.78 mmol) followed after 10 min by methyl iodide (0.1 ml). After 16 h, a further amount of sodium hydride (8 mg) and methyl iodide (0.1 ml) were added. After 3 h, the mixture was diluted with water, extracted with ethyl acetate, the extracts washed with water, dried over sodium sulphate and evaporated to give the sub-title compound as a pale yellow solid (213 mg).

Workup

  1. waitAfter 3 h
  2. extractionextracted with ethyl acetate
  3. washthe extracts washed with water
  4. dry with materialdried over sodium sulphate
  5. customevaporated

Sources & evidence

ORD record
ord-82de133bdae441a29199798474105bd8
Source dataset
uspto-grants-2007_10
Patent number
US07276528B2

Reaction notes

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