Phenyl isocyanate → HCID 58976180, compound

HRID 1179266Notes

Reaction equation

HRID 1179266 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([NH:7][C:8]2[N:12]=[C:11]([NH2:13])[NH:10][N:9]=2)[CH:2]=1.[C:14]1([N:20]=[C:21]=[O:22])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C1COCC1.C(Cl)Cl>[C:14]1([NH:20][C:21]([N:10]2[C:11]([NH2:13])=[N:12][C:8]([NH:7][C:3]3[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=3)=[N:9]2)=[O:22])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 2

HCID 7672Phenyl isocyanateHCID 13789693HCID 13789693, compound

Product 1

HCID 58976180HCID 58976180, compoundYield 17.3%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N3-(3-pyridyl)-1H-[1,2,4]triazole-3,5-diamine (0.43 mmol) in dry THF (3 mL) and dry DCM (3 mL) was added phenylisocyanate (0.43 mmol) dropwise over 1 minute, and the mixture was stirred at room temperature for 2 hours. The reaction mixture was concentrated in vacuo and the residue purified by column chromatography [Merck silica, eluted with EtOAc and Hexanes (4:1)] to afford compound the title compound (22.0 mg, 17%). 1H NMR (400 MHz, DMSO-d6) 7.17 (1H, t), 7.28 (1H, m), 7.39 (4H, m), 7.65 (2H, d), 8.09 (1H, m), 8.23 (1H, m), 8.79 (1H, d), 9.44 (1H, s), 9.64 (1H, s); MS (ES+): m/e=296.3 (100%).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe residue purified by column chromatography [Merck silica, eluted with EtOAc and Hexanes (4:1)]

Sources & evidence

ORD record
ord-2803747cb70f4565be509143e41ed0ae
Source dataset
uspto-grants-2007_10
Patent number
US07279469B2

Reaction notes

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