Ethanol → HCID 86164042, compound

HRID 1068301Notes

Reaction equation

HRID 1068301 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Si:8]([CH3:11])([CH3:10])[CH3:9])[C:3]=1[N:12]=[C:13]=[O:14].[CH2:15]([OH:17])[CH3:16]>>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Si:8]([CH3:10])([CH3:11])[CH3:9])[C:3]=1[NH:12][C:13](=[O:14])[O:17][CH2:15][CH3:16]

Participants

3

Reactant 2

HCID 702EthanolHCID 18630278HCID 18630278, compound

Product 1

HCID 86164042HCID 86164042, compound

Procedure

A mixture of the compound of Example h (10 mmol) and ethanol (75 mL) was refluxed for 1 h. The mixture was concentrated and the residue dissolved in ethyl acetate. The solution was washed twice with water and the solvent removed to yield the crude product, which was recrystallized from hexane. GC/MS showed some remaining isocyanate so the solid was dissolved in ethanol and refluxed again with approx. 0.1 g diazobisbicyclooctane. FID/GC indicated a complete reaction and the ethanol was removed and the title compound recovered. m.p. 109-110° C.

Workup

  1. temperaturewas refluxed for 1 h
  2. concentrationThe mixture was concentrated
  3. dissolutionthe residue dissolved in ethyl acetate
  4. washThe solution was washed twice with water
  5. customthe solvent removed

Sources & evidence

ORD record
ord-a28bf1c93e324808bf32af31408c32eb
Source dataset
uspto-grants-2001_06
Patent number
US06248894B1

Reaction notes

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