Benzyl isocyanate → HCID 17943125, compound

HRID 483377Notes

Reaction equation

HRID 483377 reaction equation
[CH2:1]([N:8]=[C:9]=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH:11][CH:12]([CH2:17][C:18]1[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][CH:19]=1)[C:13]([O:15]C)=O>C1(C)C=CC=CC=1>[CH2:1]([N:8]1[C:13](=[O:15])[CH:12]([CH2:17][C:18]2[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][CH:19]=2)[O:11][C:9]1=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 76639Benzyl isocyanateHCID 11075076HCID 11075076, compound

Product 1

HCID 17943125HCID 17943125, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Benzyl isocyanate (1.2 g, Aldrich) was added at room temperature to a stirred solution of the product from step (b) (2.03 g) in toluene (25 ml). When addition was complete, the mixture was refluxed for 40 hours. The toluene was evaporated in vacuo and the residue flash chromatographed through a silica column using chloroform to give the desired product as a colourless oil which crystallised on standing (2.9 g). The product was recrystallised from IPA as fine white needles (1.8 g), mp 92°-93° C. The 200 MHz 1H NMR was consistent with the proposed structure.

Workup

  1. additionWhen addition
  2. temperaturethe mixture was refluxed for 40 hours
  3. customThe toluene was evaporated in vacuo
  4. customthe residue flash chromatographed through a silica column

Sources & evidence

ORD record
ord-1680a5766d424555b4c48cb35c11f196
Source dataset
uspto-grants-1993_07
Patent number
US05225431

Reaction notes

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