Ethanol → HCID 86164042, compound

HRID 1458075Notes

Reaction equation

HRID 1458075 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 he solvent removed to yield the crude product, which as 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 and he solvent
  5. customremoved

Sources & evidence

ORD record
ord-916ce8af673d460689dfc022110bc298
Source dataset
uspto-grants-1998_12
Patent number
US05849723

Reaction notes

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