Phenyl isocyanate → HCID 10813316, compound

HRID 1636402Notes

Reaction equation

HRID 1636402 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-cyanophenoxy)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-c46e5e1c561a4092ba93cb7155c4c68a
Source dataset
uspto-grants-2000_03
Patent number
US06034103

Reaction notes

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