Benzyl isocyanate → HCID 15818790, compound

HRID 439341Notes

Reaction equation

HRID 439341 reaction equation
[C:1]([C:3]1[CH:12]=[C:11]2[C:6]([C:7]([CH3:23])([CH3:22])[CH2:8][CH2:9][N:10]2[C:13]([NH:15]C2C=CC=CC=2)=[O:14])=[CH:5][CH:4]=1)#[N:2].[CH2:24](N=C=O)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>CN(C)C1C=CN=CC=1.C(#N)C>[C:1]([C:3]1[CH:12]=[C:11]2[C:6]([C:7]([CH3:22])([CH3:23])[CH2:8][CH2:9][N:10]2[C:13]([NH:15][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[O:14])=[CH:5][CH:4]=1)#[N:2]

Participants

5

Reactant 2

HCID 76639Benzyl isocyanateHCID 9948447HCID 9948447, compound

Product 1

HCID 15818790HCID 15818790, compoundYield 87.8%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6342AcetonitrileSolvent

Procedure

A solution of the title J compound from Example 1 (0.20 g, 1.07 mmole), benzyl isocyanate (0.14 g, 1.07 mmole) and 4-dimethylaminopyridine (50 mg) in acetonitrile (4.5 mL) was heated under argon at reflux for one hour. The solvent was recovered under vacuum and the crude product was chromatographed on silica eluting with hexane/ethyl acetate (7:3) to afford 0.30 g of the title compound as a white solid; m.p. 114°-115° C.

Workup

  1. temperatureat reflux for one hour
  2. customThe solvent was recovered under vacuum
  3. customthe crude product was chromatographed on silica eluting with hexane/ethyl acetate (7:3)

Sources & evidence

ORD record
ord-bb67d91e7d064573ad46744ff8b213fa
Source dataset
uspto-grants-1996_05
Patent number
US05514690

Reaction notes

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