1,2-Epoxybutane → HCID 19737720, compound

HRID 258373Notes

Reaction equation

HRID 258373 reaction equation
[C:1]1([NH:7][C:8]#[N:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[O:10]1[CH:12]([CH2:13][CH3:14])[CH2:11]1.C(=O)([O-])[O-].[K+].[K+]>C(C(C)=O)C>[NH:9]=[C:8]1[N:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH2:11][CH:12]([CH2:13][CH3:14])[O:10]1

Participants

5

Reactant 3

HCID 78341,2-EpoxybutaneHCID 11430Potassium CarbonateHCID 69318Phenylcyanamide

Product 1

HCID 19737720HCID 19737720, compound

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

In a flask were combined 3.0 grams (g) (25.4 mmol) phenyl cyanamide, 1.83 g (25.4 mmol) 1,2-epoxy butane, 3.51 g (25.4 mmol) potassium carbonate and 50 milliliters (ml) methyl ethyl ketone. The mixture was stirred overnight under a nitrogen blanket at room temperature. It was then filtered and the methyl ethyl ketone removed in vacuo. The solids recovered from the filter were extracted with acetone and combined with the residue from the main portion. The combined solids were dissolved in water and extraced with 15% isopropanol in chloroform. The solvents were removed in vacuo producing 2.30 g (48% of theoretical yield) of the desired product. Spectroscopic analysis confirmed the structure of the desired product. No type II product was detected.

Workup

  1. customIn a flask were combined
  2. filtrationIt was then filtered
  3. customthe methyl ethyl ketone removed in vacuo
  4. customThe solids recovered from the filter
  5. extractionwere extracted with acetone
  6. dissolutionThe combined solids were dissolved in water
  7. customThe solvents were removed in vacuo
  8. customproducing

Sources & evidence

ORD record
ord-580cc170fb7d4f6db281576fdfd83fb5
Source dataset
uspto-grants-1993_11
Patent number
US05266701

Reaction notes

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