Methyl iodide → HCID 70087190, compound

HRID 1533776Notes

Reaction equation

HRID 1533776 reaction equation
[CH3:1][C:2]1([CH3:28])[N:6]=[C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[NH:13][C:14](=[O:27])[C:15]2[CH:20]=[CH:19][C:18]([C:21]([O:23][CH3:24])=[O:22])=[C:17]([O:25][CH3:26])[CH:16]=2)[O:4][CH2:3]1.[H-].[Na+].[CH3:31]I>CN(C)C=O>[CH3:1][C:2]1([CH3:28])[N:6]=[C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[N:13]([CH3:31])[C:14](=[O:27])[C:15]2[CH:20]=[CH:19][C:18]([C:21]([O:23][CH3:24])=[O:22])=[C:17]([O:25][CH3:26])[CH:16]=2)[O:4][CH2:3]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 57240070HCID 57240070, compound

Product 1

HCID 70087190HCID 70087190, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of N-[2-(4,4-dimethyl(2,5-oxazolinyl)]-phenyl]-3-methoxy-4-methoxycarbonylbenzamide (1.45 g) in N,N-dimethylformamide (18 ml) was added portionwise sodium hydride (167 mg) at 0° C. and the mixture was stirred at 0° C. for 30 minutes. Methyl iodide (0.283 ml) was added to the mixture and the solution was stirred at 0° C. for 1 hour. The reaction was quenched with water and then the aqueous solution was extracted with ethyl acetate. The organic layer was washed with brine and dried over sodium sulfate. The solvent was evaporated in vacuo to give N-[2-[4,4-dimethyl-(2,5-oxazolinyl)]phenyl]-N-methyl-3-methoxy-4-methoxycarbonylbenzamide (1.5 g).

Workup

  1. stirringthe solution was stirred at 0° C. for 1 hour
  2. customThe reaction was quenched with water
  3. extractionthe aqueous solution was extracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over sodium sulfate
  6. customThe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-801df7e35c3b429a9746f0c8c819a521
Source dataset
uspto-grants-2001_03
Patent number
US06207693B1

Reaction notes

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