Benzyl isocyanate → HCID 15291499, compound

HRID 1609698Notes

Reaction equation

HRID 1609698 reaction equation
[C:1]([C:3]1[CH:11]=[C:10]2[C:6]([C:7]([CH3:23])([CH3:22])[CH2:8][CH:9]2[NH:12][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>C(O)C>[C:1]([C:3]1[CH:11]=[C:10]2[C:6]([C:7]([CH3:23])([CH3:22])[CH2:8][CH:9]2[NH:12][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

4

Reactant 2

HCID 76639Benzyl isocyanateHCID 10063698HCID 10063698, compound

Product 1

HCID 15291499HCID 15291499, compoundYield 126.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 3-amino-5-cyano-1,1-dimethylindane (0.40 g, 2.15 mmol, prepared according to part F of Example 6) and benzyl isocyanate (0.29 g, 2.15 mmole) in ethanol (3.5 ml) under argon was heated at reflux for three hours. The solvent was recovered under vacuum to obtain 0.87 g of yellow gum. The crude product was chromatographed on silica eluting with 1:1 ethyl acetate/hexane to obtain an amorphous white solid (0.44 g). The chromatogrpahy isolate was further purified by crystallization from isopropyl ether to afford the title compound as a pure white solid (0.40 g), m.p. 130°-132° C. 1H NMR δ 7.71 (d, J=8.21 Hz, 1H), 7.52 (s, 1H), 7.44 (d, J=7.63 Hz, 1H), 7.31 (m, 5H), 6.44 (m, 2H), 5.22 (m, 1H), 4.28 (d, J=5.86, 2H), 2.30 (dd, J=7.04, 12.90 Hz, 1H), 1.71 (dd, J=9.38, 12.31 Hz, 1H), 1.35 (s, 3H), 1.17 (s, 3H); 13C NMR δ 157.97, 156.88, 145.38, 140.75, 131.88, 128.19, 127.59, 126.98, 126.58, 123.50, 119.06, 109.33, 52.06, 48.74, 42.98, 42.00, 28.64, 28.21.

Workup

  1. temperatureat reflux for three hours
  2. customThe solvent was recovered under vacuum

Sources & evidence

ORD record
ord-33bfb6f178534085a353d174efa55c3b
Source dataset
uspto-grants-1995_03
Patent number
US05401848

Reaction notes

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