Methyl iodide → HCID 18938975, compound

HRID 356637Notes

Reaction equation

HRID 356637 reaction equation
[CH3:1][S:2]([NH:5][C:6]1[CH:7]=[CH:8][C:9]([O:17][CH3:18])=[C:10]([CH:12]2[O:16][CH2:15][CH2:14][O:13]2)[CH:11]=1)(=[O:4])=[O:3].[H-].[Na+].[CH3:21]I.[Cl-].[NH4+]>CN(C=O)C>[CH3:21][N:5]([C:6]1[CH:7]=[CH:8][C:9]([O:17][CH3:18])=[C:10]([CH:12]2[O:13][CH2:14][CH2:15][O:16]2)[CH:11]=1)[S:2]([CH3:1])(=[O:3])=[O:4]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 18938966HCID 18938966, compound

Product 1

HCID 18938975HCID 18938975, compoundYield 113.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 2-(5-methylsulfonylamino-2-methoxyphenyl)-1,3-dioxolane (8.63 g, 31.6 mmol) in DMF (30 ml) was added NaH (1.51 g, 37.9 mmol) and methyl iodide (2.36 ml, 37.9 mmol) and then stirred at 60° C. for 1 hr. After aqueous ammonium chloride was added to the reaction mixture, the mixture was extracted with ether/CH2Cl2. The extract was dried over MgSO4 and evaporated in vacuo to give crude 2-[5-(N-methyl-N-methylsulfonylamino)-2-methoxyphenyl]-1,3-dioxolane (10.29 g) as a brown oil.

Workup

  1. extractionthe mixture was extracted with ether/CH2Cl2
  2. dry with materialThe extract was dried over MgSO4
  3. customevaporated in vacuo

Sources & evidence

ORD record
ord-3a124250e2c0478689e5f7fd4831c581
Source dataset
uspto-grants-1998_11
Patent number
US05837711

Reaction notes

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