Methyl iodide → HCID 18753499, compound

HRID 1838427Notes

Reaction equation

HRID 1838427 reaction equation
[C:1](=O)([O-])[O-].[K+].[K+].[O:7]([C:14]1[CH:19]=[CH:18][C:17]([S:20]([NH:23][CH:24]([CH2:27][OH:28])[CH2:25][OH:26])(=[O:22])=[O:21])=[CH:16][CH:15]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.CI>CN(C)C=O>[CH3:1][N:23]([S:20]([C:17]1[CH:18]=[CH:19][C:14]([O:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:15][CH:16]=1)(=[O:22])=[O:21])[CH:24]([CH2:25][OH:26])[CH2:27][OH:28]

Participants

5

Reactant 3

HCID 6328Methyl iodide2×HCID 11430Potassium CarbonateHCID 18753581HCID 18753581, compound2×

Product 1

HCID 18753499HCID 18753499, compoundYield 75.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

After potassium carbonate (45.39 g, 328.4 mmol) was added to a solution of N-(4-phenoxybenzenesulfonyl)serinol (10.62 g, 32.84 mmol), the product of (1) above, in N,N-dimethylformamide (250 ml), methyl iodide (5.12 g, 36.12 mmol) was added dropwise to the mixture. After stirring it at room temperature for 2 hours, the same amount of methyl iodide was further added to this mixture and stirred for 1 hour. The solvent of the reaction mixture was evaporated under reduced pressure, ice-water was added to the resulting residue and this was extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous magnesium sulfate and concentrated under reduced pressure to afford the desired compound (8.32 g, yield 75%) as a white powder.

Workup

  1. stirringstirred for 1 hour
  2. customThe solvent of the reaction mixture was evaporated under reduced pressure, ice-water
  3. additionwas added to the resulting residue
  4. extractionthis was extracted with ethyl acetate
  5. washThe organic layer was washed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ce33a9e39bdd4e608fd8f0201d36d7a5
Source dataset
uspto-grants-2004_01
Patent number
US06673804B1

Reaction notes

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