Phenyl isocyanate → HCID 47448403, compound

HRID 131673Notes

Reaction equation

HRID 131673 reaction equation
Cl.[N+](C1C=C(C=CC=1)CN)([O-])=O.[N+:13]([C:16]1[CH:17]=[C:18]([CH:30]=[CH:31][CH:32]=1)[CH2:19][NH:20][C:21]([NH:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:22])([O-:15])=[O:14].C(N(CC)CC)C.C1(N=C=O)C=CC=CC=1>C(O)C>[N+:13]([C:16]1[CH:17]=[C:18]([CH:30]=[CH:31][CH:32]=1)[CH2:19][NH:20][C:21]([NH:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:22])([O-:15])=[O:14]

Participants

5

Reactant 3

HCID 7672Phenyl isocyanateHCID 8471TriethylamineHCID 86760687HCID 86760687, compound

Product 1

HCID 47448403HCID 47448403, compoundYield 95.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

N-(3-Nitrobenzyl)-N′-phenylurea 3-Nitrobenzylamine hydrochloride (377 mg, 2.0 mmol) and triethylamine (278 μl, 2 mmol) were stirred in ethanol (5 ml) for 15 min. Phenylisocyanate (230 μl, 2.12 mmol) was added dropwise to the solution and stirring continued for 45 min at room temperature once the addition was complete. The reaction was concentrated under vacuum and the residue partitioned between ethyl acetate and water. The organic phase was washed with water, dried (sodium sulphate) and the solvent evaporated under vacuum to give N-(3-nitrobenzyl)-N′-phenylurea (520 mg). MP; 153-156° C.

Workup

  1. additiononce the addition
  2. concentrationThe reaction was concentrated under vacuum
  3. customthe residue partitioned between ethyl acetate and water
  4. washThe organic phase was washed with water
  5. dry with materialdried (sodium sulphate)
  6. customthe solvent evaporated under vacuum

Sources & evidence

ORD record
ord-f6679c34ee5f4cbca2bee3a8c1c4342b
Source dataset
uspto-grants-2008_06
Patent number
US07384963B2

Reaction notes

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