Diphenyl N-Cyanocarbonimidate → HCID 18184813, compound

HRID 2229413Notes

Reaction equation

HRID 2229413 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:12][CH:11]=[N:10][CH:9]=2)=[C:4]([O:13][CH3:14])[CH:3]=1.[CH:15]1[CH:20]=[CH:19][C:18]([O:21][C:22](OC2C=CC=CC=2)=[N:23][C:24]#[N:25])=[CH:17][CH:16]=1>C(#N)C>[C:18]1([O:21][C:22](=[N:1][C:2]2[CH:7]=[CH:6][C:5]([C:8]3[O:12][CH:11]=[N:10][CH:9]=3)=[C:4]([O:13][CH3:14])[CH:3]=2)[NH:23][C:24]#[N:25])[CH:19]=[CH:20][CH:15]=[CH:16][CH:17]=1

Participants

4

Reactant 2

HCID 688090Diphenyl N-CyanocarbonimidateHCID 154627323-Methoxy-4-(oxazol-5-yl)aniline

Product 1

HCID 18184813HCID 18184813, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 1D (0.200 g, 1.05 mmol) and diphenyl cyanocarbonimidate (0.258 g, 1.05 mmol) in 10 mL of acetonitrile was stirred at reflux for 40 h. As the reaction mixture cooled to room temperature, a yellow solid precipitated out of solution. The volume of solvent was reduced by half, and ether was added. Vacuum filtration afforded 0.330 g (94%) of 15A as a pale yellow solid which was 97% pure by LC/MS (retention time=3.48 min.; M+=335.15. 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. temperatureat reflux for 40 h
  2. customa yellow solid precipitated out of solution
  3. additionwas added
  4. filtrationVacuum filtration

Sources & evidence

ORD record
ord-51e4eadca32d4aed80968246293e7e5e
Source dataset
uspto-grants-2002_07
Patent number
US06420403B1

Reaction notes

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