Methyl iodide → HCID 18703989, compound

HRID 2288067Notes

Reaction equation

HRID 2288067 reaction equation
[CH3:1][S:2]([NH:5][CH:6]1[CH2:15][C:14]([CH3:17])([CH3:16])[CH2:13][C:12]2[C:11]([C:18]([O:20][CH3:21])=[O:19])=[CH:10][CH:9]=[CH:8][C:7]1=2)(=[O:4])=[O:3].[H-].[Na+].I[CH3:25]>CN(C=O)C>[CH3:1][S:2]([N:5]([CH3:25])[CH:6]1[CH2:15][C:14]([CH3:17])([CH3:16])[CH2:13][C:12]2[C:11]([C:18]([O:20][CH3:21])=[O:19])=[CH:10][CH:9]=[CH:8][C:7]1=2)(=[O:4])=[O:3]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 18703994HCID 18703994, compound

Product 1

HCID 18703989HCID 18703989, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 0.5 g (1.6 mmol) of methyl 5-methanesulfonylamino-7,7-dimethyl-5,6,7,8-tetrahydro-1-naphthalenecarboxylate in 5 ml of DMF was added dropwise to a suspension of 0.05 g (1.8 mmol) of 80 percent sodium hydride in 4 ml of DMF. After stirring at room temperature for 1 hr., 0.23 g (1.6 mmol) of iodomethane was added and the mixture was stirred at room temperature for 4 h. The reaction mixture was completely concentrated in vacuo and the residue was then taken up in EA and water and the organic phase was washed with dilute hydrochloric acid and sodium bicarbonate solution. After drying over magnesium sulfate and concentrating in vacuo; 0.5 g of methyl 5-(methanesulfonyl-methyl-amino)-7,7-dimethyl-5,6,7,8-tetrahydronaphthalene-1-carboxylate was obtained; m.p. 98-99° C.

Workup

  1. stirringthe mixture was stirred at room temperature for 4 h
  2. concentrationThe reaction mixture was completely concentrated in vacuo
  3. washwater and the organic phase was washed with dilute hydrochloric acid and sodium bicarbonate solution
  4. dry with materialAfter drying over magnesium sulfate
  5. concentrationconcentrating in vacuo

Sources & evidence

ORD record
ord-f1f151a54dcd48dfb0458c76c0770eaf
Source dataset
uspto-grants-2000_07
Patent number
US06087399

Reaction notes

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