Ethanol → Diisopropyl ether ethanol

HRID 1582613Notes

Reaction equation

HRID 1582613 reaction equation
FC(F)(F)C1C=CC(CN([C:12]2[CH:17]=[CH:16]C(C#N)=CC=2)N)=CC=1.CO[CH:24]([O:29]C)[CH2:25]N=C=S.[CH2:31]([OH:33])[CH3:32]>>[CH:24]([O:29][CH:17]([CH3:16])[CH3:12])([CH3:31])[CH3:25].[CH2:31]([OH:33])[CH3:32]

Participants

4

Reactant 3

HCID 702EthanolHCID 144710Isothiocyanatoacetaldehyde dimethyl acetalHCID 12985733N1-(4-trifluoromethylphenylmethyl)-N1-(4-cyanophenyl)hydrazine

Product 1

HCID 23358034Diisopropyl ether ethanol

Procedure

To a suspension of N1-(4-trifluoromethylphenylmethyl)-N1-(4-cyanophenyl)hydrazine (7.5 g, 0.025 mol) in ethanol (100 ml) was added dropwise 2,2-dimethoxyethylisothiocyanate (4 g, 0.027 mol) and the reaction mixture was heated to reflux for 2 h. After cooling the solvent was evaporated under vacuum, the resulting residue was poured into 2N H2SO4 (20 ml) and the suspension was heated to reflux for 0.3 h. After extraction with ethyl acetate, the organic layer was washed with water, dried over sodium sulfate and concentrated under vacuum. Flash chromatography on silica gel (toluene/dioxane: 8/2) and trituration from diisopropyl ether/ethanol afforded a yellow solid (2.7 g, 28%), mp 200° C.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureto reflux for 2 h
  3. temperatureAfter cooling the solvent
  4. customwas evaporated under vacuum
  5. additionthe resulting residue was poured into 2N H2SO4 (20 ml)
  6. temperaturethe suspension was heated
  7. temperatureto reflux for 0.3 h
  8. extractionAfter extraction with ethyl acetate
  9. washthe organic layer was washed with water
  10. dry with materialdried over sodium sulfate
  11. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-d32030b38bc64f40ab0975509e3cee5b
Source dataset
uspto-grants-2004_05
Patent number
US06737433B1

Reaction notes

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