Tetrahydrofuran → 1,2-Epoxy-3-[5-(hex-5-enylaminocarbonyl)thiazol-2-yloxy]propane

HRID 461841Notes

Reaction equation

HRID 461841 reaction equation
[H-].[Na+].O1CCCC1.[CH2:8]1[O:10][CH:9]1[CH2:11][OH:12].C(S([C:17]1[S:18][C:19]([C:22]([NH:24][CH2:25][CH2:26][CH2:27][CH2:28][CH:29]=[CH2:30])=[O:23])=[CH:20][N:21]=1)=O)C>O.C(OCC)(=O)C>[O:10]1[CH:9]([CH2:11][O:12][C:17]2[S:18][C:19]([C:22]([NH:24][CH2:25][CH2:26][CH2:27][CH2:28][CH:29]=[CH2:30])=[O:23])=[CH:20][N:21]=2)[CH2:8]1

Participants

7

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 11164GlycidolHCID 24758Sodium hydrideHCID 213919722-Ethylsulfinyl-5-(hex-5-enylaminocarbonyl)thiazole

Product 1

HCID 213927281,2-Epoxy-3-[5-(hex-5-enylaminocarbonyl)thiazol-2-yloxy]propane

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-5 °C

Procedure

In this preparation 0.0525 mole of sodium hydride in a 50% mineral oil mixture is stirred in 300 ml. of anhydrous tetrahydrofuran, under nitrogen, then cooled to -30° C and 0.055 mole of glycidol is added dropwise. The mixture is allowed to warm to -5° C and stirred for ten minutes and then recooled to -30° C. A solution of 0.05 mole of 2-ethylsulfinyl-5-(hex-5-enylaminocarbonyl)thiazole in 100 ml. of anhydrous tetrahydrofuran is added dropwise and the resulting mixture allowed to warm to 0° C. Additional solvent is added as needed to facilitate stirring. The mixture is maintained for 30 minutes at 0° C and then poured into 500 ml. of ethyl acetate, extacted with 100 ml. of water, and then with 100 ml. of aqueous saturated sodium chloride and dried over anhydrous magnesium sulfate and filtered. The filtrate is evaporated under vacuum affording an oily residue which is then further purified by chromatography on silica gel eluting with 40% ethyl acetate-60% hexane, by vol., affording 1,2-epoxy-3-[5-(hex-5-enylaminocarbonyl)thiazole-2-yloxy]propane.

Workup

  1. stirringstirred for ten minutes
  2. customrecooled to -30° C
  3. temperatureto warm to 0° C
  4. additionAdditional solvent is added
  5. stirringto facilitate stirring
  6. temperatureThe mixture is maintained for 30 minutes at 0° C
  7. additionpoured into 500 ml
  8. dry with materialof aqueous saturated sodium chloride and dried over anhydrous magnesium sulfate
  9. filtrationfiltered
  10. customThe filtrate is evaporated under vacuum
  11. customaffording an oily residue which
  12. customis then further purified by chromatography on silica gel eluting with 40% ethyl acetate-60% hexane, by vol.

Sources & evidence

ORD record
ord-5efe075ba2f744aeab0def10816024f0
Source dataset
uspto-grants-1977_12
Patent number
US04064259

Reaction notes

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