Thiophenol → HCID 15045499, compound

HRID 1090650Notes

Reaction equation

HRID 1090650 reaction equation
Cl[CH2:2][CH:3]1[S:11][C:10]2[N:5]([C:6](=[O:16])[N:7]([CH2:13][CH2:14][CH3:15])[C:8](=[O:12])[CH:9]=2)[CH2:4]1.[C:17]1([SH:23])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C(=O)([O-])[O-].[K+].[K+]>C(O)C.C(Cl)Cl.O>[C:17]1([S:23][CH2:2][CH:3]2[S:11][C:10]3[N:5]([C:6](=[O:16])[N:7]([CH2:13][CH2:14][CH3:15])[C:8](=[O:12])[CH:9]=3)[CH2:4]2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

7

Reactant 3

HCID 7969ThiophenolHCID 11430Potassium CarbonateHCID 15027662HCID 15027662, compound

Product 1

HCID 15045499HCID 15045499, compoundYield 95%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 2-chloromethyl-6-propyl-2,3-dihydro-5H-thiazolo[3,2-c]pyrimidine-5,7(6H)-dione (0.8 g), thiophenol (0.47 ml) and potassium carbonate (0.63 g) was refluxed in ethanol (20 ml) for 42 hours. The solution was concentrated to dryness, and the resulting residue thus obtained was dissolved in methylene chloride and water. After washing with water and drying, the organic solution was concentrated to dryness. The resulting syrup was purified by column chromatography on silica gel to give colorless syrup. This syrup was allowed to stand in a refrigerator to obtain colorless crystals (1.2 g, 95%).

Workup

  1. concentrationThe solution was concentrated to dryness
  2. customthe resulting residue thus obtained
  3. washAfter washing with water
  4. customdrying
  5. concentrationthe organic solution was concentrated to dryness
  6. customThe resulting syrup was purified by column chromatography on silica gel
  7. customto give colorless syrup

Sources & evidence

ORD record
ord-177a3a40e068454ea23e8f0f5794d380
Source dataset
uspto-grants-1992_01
Patent number
US05082838

Reaction notes

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