2-(Chloromethyl)-2-methyloxirane → HCID 14698772, compound

HRID 2066816Notes

Reaction equation

HRID 2066816 reaction equation
[O-:1][C:2]#[N:3].[K+].[Cl:5][CH2:6][C:7]1([CH3:10])[CH2:9][O:8]1>O>[Cl:5][CH2:6][C:7]1([CH3:10])[O:8][C:2](=[O:1])[NH:3][CH2:9]1

Participants

4

Reactant 2

HCID 952202-(Chloromethyl)-2-methyloxiraneHCID 11378442Potassium cyanate

Product 1

HCID 14698772HCID 14698772, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Potassium cyanate (7.61 g) was dissolved in 350 ml of water, and 2-(chloromethyl)-2-methyloxirane was slowly added (5.00 g). The solution was stirred overnight (15 h) at reflux. The reaction mixture was then extracted while still moderately warm with ethyl acetate (5×200 ml). The combined organic layers were dried over sodium sulfate and concentrated in vacuo to provide the title compound an off-white solid (3.32 g, 47%). Mass spectrum (ESI) 150.0 (M+1). 1H NMR (500 MHz, CDCl3): δ 5.23 (bs, 1H), 3.70 (d, J=8.7 Hz, 1H), 3.68 (d, J=11.0 Hz, 1H), 3.56 (d, J=11.2 Hz, 1H), 3.34 (d, J=8.9 Hz, 1H), 1.59 (s, 3H).

Workup

  1. temperatureat reflux
  2. extractionThe reaction mixture was then extracted
  3. temperaturewhile still moderately warm with ethyl acetate (5×200 ml)
  4. dry with materialThe combined organic layers were dried over sodium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5b5ada49e86c4a5ba124bb26aa51a9e6
Source dataset
uspto-grants-2012_10
Patent number
US08293721B2

Reaction notes

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