3-Isocyanatobenzonitrile → HCID 12083177, compound

HRID 1167073Notes

Reaction equation

HRID 1167073 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:7]=[CH:8][C:9]=1[C:10]1[O:14][CH:13]=[N:12][CH:11]=1)[NH2:6].[C:15]([C:17]1[CH:18]=[C:19]([N:23]=[C:24]=[O:25])[CH:20]=[CH:21][CH:22]=1)#[N:16]>C(Cl)Cl>[C:15]([C:17]1[CH:18]=[C:19]([NH:23][C:24]([NH:6][C:5]2[CH:7]=[CH:8][C:9]([C:10]3[O:14][CH:13]=[N:12][CH:11]=3)=[C:3]([O:2][CH3:1])[CH:4]=2)=[O:25])[CH:20]=[CH:21][CH:22]=1)#[N:16]

Participants

4

Reactant 2

HCID 27333153-IsocyanatobenzonitrileHCID 154627323-Methoxy-4-(oxazol-5-yl)aniline2×

Product 1

HCID 12083177HCID 12083177, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-Methoxy-4-(5-oxazolyl)aniline, 1D (1.00 g, 5.26 mmol) and 3-cyanophenyl isocyanate (1.17 g, 7.89 mmol) in DCM (40 mL) were stirred at rt for 20 h. The precipitate formed was collected by filtration, followed by washing with dichlorometnane to provide 1E (1.57 g, 89% yield) as a yellow solid. (LC/MS retention time=3.67 min.; M+=335. Column: YMC S5 ODS 4.6×5.0 mm Ballistic. Solvent A=10% MeOH, 90% H2O, 0.1% TFA; Solvent B=90% MeOH, 10% H2O, 0.1% TFA).

Workup

  1. customThe precipitate formed
  2. filtrationwas collected by filtration
  3. washby washing with dichlorometnane

Sources & evidence

ORD record
ord-9d81d1ed6cf14e99b03e74321c2d287b
Source dataset
uspto-grants-2003_09
Patent number
US06617323B2

Reaction notes

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