Acetonitrile → Phenylurea

HRID 444707Notes

Reaction equation

HRID 444707 reaction equation
[NH:1]1CCCN1C(O)=O.CC#N.[C:12]1([N:18]=[C:19]=[O:20])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>C(Cl)Cl>[C:12]1([NH:18][C:19]([NH2:1])=[O:20])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 7672Phenyl isocyanateHCID 22591521HCID 22591521, compound

Product 1

HCID 6145PhenylureaYield 247.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of azaproline VI (20.0 mg, 0.056 mmol) and TEA (9.5 pt, 0.068 mmol) in DCM (400 μL)/MeCN (750 μL) was added phenylisocyanate (7.3 μL, 0.067 mmol). The solution was stirred at rt for 16 h then concentrated in vacuo. The crude residue was purified by silica gel chromatography (ethyl acetate-hexanes) to afford 18.9 mg of phenylurea in 71% yield. LCMS (M+1): 474.84.

Workup

  1. concentrationthen concentrated in vacuo
  2. customThe crude residue was purified by silica gel chromatography (ethyl acetate-hexanes)

Sources & evidence

ORD record
ord-e143fdfe61a042b4b6b84ea4d5218577
Source dataset
uspto-grants-2013_07
Patent number
US08476225B2

Reaction notes

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