Methyl iodide → HCID 89488067, compound

HRID 570758Notes

Reaction equation

HRID 570758 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([C:8]([F:17])([C:13]([F:16])([F:15])[F:14])[C:9]([F:12])([F:11])[F:10])[CH:5]=[C:4]([Br:18])[C:3]=1[NH:19][C:20](=[O:32])[C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([N+:27]([O-:29])=[O:28])[C:22]=1[O:30][CH3:31].[H-].[Na+].I[CH3:36]>CN(C)C=O>[Br:1][C:2]1[CH:7]=[C:6]([C:8]([F:17])([C:9]([F:10])([F:11])[F:12])[C:13]([F:15])([F:16])[F:14])[CH:5]=[C:4]([Br:18])[C:3]=1[N:19]([CH3:36])[C:20](=[O:32])[C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([N+:27]([O-:29])=[O:28])[C:22]=1[O:30][CH3:31]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 89488452HCID 89488452, compound

Product 1

HCID 89488067HCID 89488067, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of N-[2,6-dibromo-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl]-2-methoxy-3-nitro-benzamide (obtained in a similar way as example I 4.1) (0.482 g, 0.806 mmole) in N,N-dimethylformamide (5 ml), magnetically stirred under argon atmosphere, at 25° C., in a round-bottomed flask, was added sodium hydride (60% suspension in oil, 0.039 g, 0.967 mmole). After the gas evolution had ceased, iodomethane (0.060 ml, 0.137 g, 0.967 mmole) was added and the mixture was stirred for 15 hours. The reaction mixture was quenched by addition of two drops of methanol, then concentrated under reduced pressure on a rotatory evaporator. The residue was placed on a silica gel column. Elution with a mixture of 15% ethyl acetate and 85% cyclohexane allowed the isolation of the title compound in quantitative yield (LC-MS analysis (method 6 described after the tables): retention time 1.22 min, observed M+H+ ion 611).

Workup

  1. stirringthe mixture was stirred for 15 hours
  2. customThe reaction mixture was quenched by addition of two drops of methanol
  3. concentrationconcentrated under reduced pressure on a rotatory evaporator
  4. washElution
  5. additionwith a mixture of 15% ethyl acetate and 85% cyclohexane

Sources & evidence

ORD record
ord-22489303cf024a289c134bb4e083d9ef
Source dataset
uspto-grants-2015_05
Patent number
US09023873B2

Reaction notes

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