Phenyl isocyanate → HCID 10813316, compound

HRID 2119518Notes

Reaction equation

HRID 2119518 reaction equation
[NH2:1][C:2]1[C:3]([O:17][C:18]2[CH:19]=[C:20]([CH:23]=[CH:24][CH:25]=2)[C:21]#[N:22])=[N:4][C:5]([O:8][C:9]2[CH:10]=[C:11]([CH:14]=[CH:15][CH:16]=2)[C:12]#[N:13])=[CH:6][CH:7]=1.[C:26]1([N:32]=[C:33]=[O:34])[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>C(#N)C>[C:21]([C:20]1[CH:19]=[C:18]([CH:25]=[CH:24][CH:23]=1)[O:17][C:3]1[C:2]([NH:1][C:33]([NH:32][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[O:34])=[CH:7][CH:6]=[C:5]([O:8][C:9]2[CH:16]=[CH:15][CH:14]=[C:11]([C:12]#[N:13])[CH:10]=2)[N:4]=1)#[N:22]

Participants

4

Reactant 2

HCID 7672Phenyl isocyanateHCID 10711354HCID 10711354, compound

Product 1

HCID 10813316HCID 10813316, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To 3,3′-[3-amino-2,6-pyridinediylbis(oxy)]bis(benzonitrile) (3.0 g, 8.7 mmol) dissolved in acetonitrile (100 mL) was added phenyl isocyanate (1.1 g, 9.5 mmol). After refluxing for 4 hours, the reaction was partitioned between ether and water. The organic layer was separated, washed with water, saturated aqueous sodium bicarbonate, and brine, dried (MgSO4), and the solvent was removed in vacuo. Chromatography on silica gel with ethyl acetate/hexane (1/4) as eluent gave material which was crystallized from ethyl acetate/hexane to give N-[2,6-bis(3-cyano-phenoxy)pyridin-3-yl]-N′-phenylurea; NMR (CDCl3) 8.65 (d,1), 7.4 (m,8), 7.1-7.3 (m,6), 6.8 (s,1), 6.7 (d,1) ppm.

Workup

  1. temperatureAfter refluxing for 4 hours
  2. customthe reaction was partitioned between ether and water
  3. customThe organic layer was separated
  4. washwashed with water, saturated aqueous sodium bicarbonate, and brine
  5. dry with materialdried (MgSO4)
  6. customthe solvent was removed in vacuo
  7. customChromatography on silica gel with ethyl acetate/hexane (1/4) as eluent gave material which
  8. customwas crystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-5443f2f0dc5b4acd906a60aa66d5d7a6
Source dataset
uspto-grants-2004_02
Patent number
US06686364B2

Reaction notes

Loading…