Methyl iodide → HCID 178470081, compound

HRID 1971779Notes

Reaction equation

HRID 1971779 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH2:9][O:10][CH3:11])[CH:6]=[C:5]([O:12][CH3:13])[C:4]=1[C:14]1[N:15]([NH:20][C:21](=[O:28])[CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])[C:16](=S)[S:17][CH:18]=1.IC>CC(C)=O>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH2:9][O:10][CH3:11])[CH:6]=[C:5]([O:12][CH3:13])[C:4]=1[C:14]1[N:15]2[N:20]=[C:21]([OH:28])[C:22]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[C:16]2[S:17][CH:18]=1

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 57912440HCID 57912440, compound

Product 1

HCID 178470081HCID 178470081, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Acetone (235 mL) was added to ethyl 3-{[4-(2,6-dimethoxy-4-(methoxymethyl)phenyl]-2-thioxo-1,3-thiazole-3(2H)-yl]-amino}-3-oxopropanoate (11.7 g, 27.6 mmol), and then iodomethane (17.1 mL, 276 mmol) was added dropwise at room temperature and the mixture was stirred for 23 hours. The solvent in the filtrate was distilled off under reduced pressure. To the obtained residue were added tert-butanol (235 mL) and potassium tert-butoxide in that order, and the mixture was stirred at room temperature for 3.5 hours. Water was added to the mixture while cooling on ice, and then aqueous 2N hydrochloric acid was added until the pH of the mixture reached approximately 4. The precipitated solid was collected by filtration, and the resulting residue was washed with water and dried under reduced pressure to obtain the title compound (6.3 g, 16 mmol).

Workup

  1. distillationThe solvent in the filtrate was distilled off under reduced pressure
  2. additionTo the obtained residue were added tert-butanol (235 mL) and potassium tert-butoxide in that order
  3. stirringthe mixture was stirred at room temperature for 3.5 hours
  4. additionWater was added to the mixture
  5. temperaturewhile cooling on ice
  6. additionaqueous 2N hydrochloric acid was added until the pH of the mixture
  7. filtrationThe precipitated solid was collected by filtration
  8. washthe resulting residue was washed with water
  9. customdried under reduced pressure

Sources & evidence

ORD record
ord-419aff0211084cea87b746d27721c23d
Source dataset
uspto-grants-2013_04
Patent number
US08431603B2

Reaction notes

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