1,4-Dioxane → HCID 21914731, compound

HRID 2117867Notes

Reaction equation

HRID 2117867 reaction equation
Cl[CH2:2][C:3]1[N:4]=[C:5]([NH:8][C:9](=[O:13])[O:10][CH2:11][CH3:12])[S:6][CH:7]=1.[O:14]1CCOCC1>O>[OH:14][CH2:2][C:3]1[N:4]=[C:5]([NH:8][C:9](=[O:13])[O:10][CH2:11][CH3:12])[S:6][CH:7]=1

Participants

4

Reactant 2

HCID 312751,4-DioxaneHCID 21914836Ethyl [4-(chloromethyl)-1,3-thiazol-2-yl]carbamate

Product 1

HCID 21914731HCID 21914731, compoundYield 98.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixed solution of ethyl 4-(chloromethyl)-1,3-thiazol-2-ylcarbamate (500 mg) in 1,4-dioxane (5 ml) and water (10 ml) was refluxed with stirring for 3.5 hours. After cooling, it was concentrated under reduced pressure. The mixture was partitioned between ethyl acetate and water. The organic phase was separated, washed with brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (10 g) using a mixed solvent of hexane and ethyl acetate (2:1). The fractions containing the objective compound were collected and evaporated under reduced pressure to give colorless syrup (450 mg, 98.2%).

Workup

  1. temperatureAfter cooling
  2. concentrationit was concentrated under reduced pressure
  3. customThe mixture was partitioned between ethyl acetate and water
  4. customThe organic phase was separated
  5. washwashed with brine
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by column chromatography on silica gel (10 g)
  9. additionThe fractions containing the objective compound
  10. customwere collected
  11. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-e711d4cf4c1b41f2aaaa89aa6168e0eb
Source dataset
uspto-grants-2008_10
Patent number
US07442715B2

Reaction notes

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