Ethanol → HCID 86164042, compound

HRID 2188098Notes

Reaction equation

HRID 2188098 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-725dcd39c0624da89149ce69273b94b2
Source dataset
uspto-grants-2002_06
Patent number
US06410558B1

Reaction notes

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