Benzyl isocyanate → HCID 54126838, compound

HRID 1609696Notes

Reaction equation

HRID 1609696 reaction equation
[NH2:1][C@@H:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([N+:11]([O-:13])=[O:12])[CH:9]=2)[C:4]([CH3:15])([CH3:14])[C@H:3]1[OH:16].[CH2:17]([N:24]=[C:25]=[O:26])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C(O)C>[OH:16][C@@H:3]1[C:4]([CH3:14])([CH3:15])[C:5]2[C:10](=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][CH:6]=2)[C@H:2]1[NH:1][C:25]([NH:24][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:26]

Participants

4

Reactant 2

HCID 76639Benzyl isocyanateHCID 67785604HCID 67785604, compound

Product 1

HCID 54126838HCID 54126838, compoundYield 94.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of trans-3-amino-1,1-dimethyl-2-hydroxy-5-nitro indane (0.75 g, 3.37 mmoles, as prepared in part H of Example 1) and benzyl isocyanate (0.45 g, 3.37 mmoles) in ethanol (6 ml) was heated at reflux for three hours and cooled to room temperature. The reaction product, which had precipitated from solution was collected by suction filtration and dried under vacuum to afford 1.13 g of the title compound as a pure white solid, m.p. 202°-204° C. 1H NMR (DMSO-d6) δ 8.14 (dd, J=2.34 and 8.21 Hz, 1H), 7.91 (s, 1H), 7.50 (d, J=8.21 Hz, 1H), 7.39-7.25 (m, 5H), 6.61 (m, 1H), 5.63 (d, J=5.28 Hz, 1H), 4.93 (dd, J=8.21 and 8.79 Hz, 1H), 4.34 (d, J=5.68 Hz, 2H), 3.79 (dd, J=5.87 and 8.79 Hz, 1H), 1.32 (s, 3H), 1.06 (s, 3H). 13H NMR (DMSO-d6) δ 158.63, 156.50, 146.85, 142.88, 140.81, 128.25, 127.01, 126.61, 123.87, 123.33, 118.66, 84.74, 57.93, 44.05, 44.07, 25.04, 22.42.

Workup

  1. temperatureat reflux for three hours
  2. customThe reaction product, which had precipitated from solution
  3. filtrationwas collected by suction filtration
  4. customdried under vacuum

Sources & evidence

ORD record
ord-b3c03a588633430197e6392b89425619
Source dataset
uspto-grants-1995_03
Patent number
US05401848

Reaction notes

Loading…