Methyl iodide → HCID 9817285, compound

HRID 2288065Notes

Reaction equation

HRID 2288065 reaction equation
[N+:1]([C:4]1[CH:13]=[C:12]2[C:7]([CH2:8][CH2:9][CH2:10][CH:11]2[NH:14][S:15]([CH3:18])(=[O:17])=[O:16])=[CH:6][CH:5]=1)([O-:3])=[O:2].[H-].[Na+].I[CH3:22]>CN(C=O)C>[CH3:22][N:14]([CH:11]1[C:12]2[C:7](=[CH:6][CH:5]=[C:4]([N+:1]([O-:3])=[O:2])[CH:13]=2)[CH2:8][CH2:9][CH2:10]1)[S:15]([CH3:18])(=[O:17])=[O:16]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 18703986HCID 18703986, compound

Product 1

HCID 9817285HCID 9817285, compoundYield 24%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 1.2 g (4.4 mmol) of N-(7-nitro-1,2,3,4-tetrahydronaphthalen-1-yl)methanesulfonamide in 16 ml of DMF was added dropwise to a suspension of 0.15 g (5.1 nmol) 80 percent sodium hydride in 10 ml of DMF. After stirring at room temperature for 1 hr., 0.62 g (4.4 mmol) of iodomethane were added and the mixture was allowed to stand at room temperature overnight. The reaction mixture was completely concentrated in vacuo and the residue was then taken up in EA and water. After washing the organic phase with dil. hydrochloric acid and sodium bicarbonate solution and concentrating, the residue was purified by chromatography on silica gel using cyclohexane/EA 3:1 and 0.3 g of N-methyl-N-(7-nitro-1,2,3,4-tetrahydronaphthalen-1-yl)methanesulfonamide was obtained; m.p. 138-140° C.

Workup

  1. waitto stand at room temperature overnight
  2. concentrationThe reaction mixture was completely concentrated in vacuo
  3. washAfter washing the organic phase with dil. hydrochloric acid and sodium bicarbonate solution
  4. concentrationconcentrating
  5. customthe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-440db1a9d9324fe7acfbe9b84040f8e6
Source dataset
uspto-grants-2000_07
Patent number
US06087399

Reaction notes

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