Dimethyl Sulfide → HCID 18707295, compound

HRID 1421986Notes

Reaction equation

HRID 1421986 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([C:13]2[S:14][CH:15]=[C:16]([C:18]3[CH:23]=[C:22]([CH2:24][C:25]([CH3:27])=C)[C:21]([O:28][CH2:29][O:30][CH3:31])=[C:20]([C:32]([O:34][CH2:35][O:36][CH2:37]OC)=[O:33])[CH:19]=3)[N:17]=2)[CH:7]=[CH:8][C:9]=1[O:10][CH2:11][CH3:12])[CH3:2].[O:40]=[O+][O-].CSC>CO>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([C:13]2[S:14][CH:15]=[C:16]([C:18]3[CH:23]=[C:22]([CH2:24][C:25](=[O:40])[CH3:27])[C:21]([O:28][CH2:29][O:30][CH3:31])=[C:20]([C:32]([O:34][CH2:35][O:36][CH3:37])=[O:33])[CH:19]=3)[N:17]=2)[CH:7]=[CH:8][C:9]=1[O:10][CH2:11][CH3:12])[CH3:2]

Participants

5

Reactant 3

HCID 1068Dimethyl SulfideHCID 24823OzoneHCID 18707227HCID 18707227, compound

Product 1

HCID 18707295HCID 18707295, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In 20 ml of methanol was dissolved 1 g of 2-(3,4-diethoxyphenyl)-4-[3-methoxymethoxymethoxycarbonyl-4-methoxymethoxy-5-(2-methyl-2-propenyl)phenyl]thiazole. Into the solution being stirred under ice-cooling was blown ozone. After 1 hour, 0.5 ml of methyl sulfide was added. The mixture was stirred at the same temperature for 30 minutes. The solvent was removed from the reaction mixture by distillation. To the residue were added 50 ml of dichloromethane and 25 ml of water. The organic layer was separated, washed with 15 ml of a saturated aqueous sodium chloride solution, dried and subjected to distillation to remove the solvent. The residue was purified by silica gel column chromatography (eluent: dichloromethane/n-hexane=2/3 by v/v) to obtain 500 mg of 2-(3,4-diethoxyphenyl)-4-(3-methoxymethoxycarbonyl-4-methoxymethoxy-5-acetylmethylphenyl)thiazole as a colorless oily substance.

Workup

  1. temperaturecooling
  2. stirringThe mixture was stirred at the same temperature for 30 minutes
  3. customThe solvent was removed from the reaction mixture by distillation
  4. additionTo the residue were added 50 ml of dichloromethane and 25 ml of water
  5. customThe organic layer was separated
  6. washwashed with 15 ml of a saturated aqueous sodium chloride solution
  7. customdried
  8. distillationsubjected to distillation
  9. customto remove the solvent
  10. customThe residue was purified by silica gel column chromatography (eluent: dichloromethane/n-hexane=2/3 by v/v)

Sources & evidence

ORD record
ord-9c8eee29ceeb4d22a03139498d6bd156
Source dataset
uspto-grants-2000_06
Patent number
US06080764

Reaction notes

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