Dimethyl Sulfate → HCID 20083093, compound

HRID 1609067Notes

Reaction equation

HRID 1609067 reaction equation
[Cl:1][C:2]1[C:3]([F:21])=[C:4]2[C:9]3=[C:10]([C:12](=[O:20])[C:13]([C:15]([O:17][CH2:18]C)=[O:16])=[CH:14][N:8]3[NH:7][CH2:6][CH2:5]2)[CH:11]=1.[CH3:22]OS(OC)(=O)=O.C(=O)([O-])[O-].[K+].[K+]>>[Cl:1][C:2]1[C:3]([F:21])=[C:4]2[C:9]3=[C:10]([C:12](=[O:20])[C:13]([C:15]([O:17][CH3:18])=[O:16])=[CH:14][N:8]3[N:7]([CH3:22])[CH2:6][CH2:5]2)[CH:11]=1

Participants

4

Reactant 3

HCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 20083133HCID 20083133, compound

Product 1

HCID 20083093HCID 20083093, compoundYield 36%

Conditions

Temperature
120 °C

Procedure

To 1.69 g (5.5 mmol) of the compound (132) obtained in Example 24, 10 ml (109 mmol) of dimethylsulfate was added, and the solution was heated at 120° C. for 4.5 hours. After air-cooling, the solution was added to 90 ml of ice/water to which 15 g (109 mmol) of anhydrous potassium carbonate was added, and the solution was stirred for 1 hour. The solution was extracted with 200 ml of chloroform, and after drying over magnesium sulfate, the solvent was removed by distillation. The residue was separated by the column chromatography (silica gel 60g, eluent solvent; chloroform: methanol=100:1) to obtain 600 mg of the subject compound (133) in a 36% yield.

Workup

  1. temperatureAfter air-cooling
  2. additionwas added
  3. extractionThe solution was extracted with 200 ml of chloroform
  4. dry with materialafter drying over magnesium sulfate
  5. customthe solvent was removed by distillation
  6. customThe residue was separated by the column chromatography (silica gel 60g, eluent solvent; chloroform: methanol=100:1)

Sources & evidence

ORD record
ord-c6613e90c16e40c4adda2aef2948b3c4
Source dataset
uspto-grants-1995_03
Patent number
US05399553

Reaction notes

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