Phenyl isocyanate → Phenylurea

HRID 860522Notes

Reaction equation

HRID 860522 reaction equation
[C:1]1([N:7]=[C:8]=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C[NH:11]S(C1C=CC(C)=CC=1)(=O)=O>ClC1C=CC=CC=1Cl>[C:1]1([NH:7][C:8]([NH2:11])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 7672Phenyl isocyanateHCID 12543Benzenesulfonamide, N,4-dimethyl-

Product 1

HCID 6145Phenylurea

Reagents, catalysts & solvents 1

HCID 72391,2-DichlorobenzeneSolvent

Procedure

Phenyl isocyanate (1.19 g, 0.01 mol) and N-methyl-4-methylbenzene sulfonamide (1.85 g, 0.01 mol) were dissolved in 1,2-dichlorobenzene (20 ml) and refluxed for 40 hrs. After cooling, the solvent was evaporated in vacuo to give a viscous oil that crystallized on standing to give N-methyl-N-4-methylphenyl-N*-phenyl urea mp 63–65° C. MS m/z 304. (M+ calcd for C15H16N2O3S=304). H NMR (300 Mhz, CDCl3) d 2.43 (s, 3, CH3), 2.65 (s, 3, CH3), 7.33 (m, 5, aromatic), 7.48 (m, 1, aromatic), 7.75 (m, 3, aromatic).

Workup

  1. temperaturerefluxed for 40 hrs
  2. temperatureAfter cooling
  3. customthe solvent was evaporated in vacuo
  4. customto give a viscous oil that
  5. customcrystallized

Sources & evidence

ORD record
ord-5938de03a2a04e439cf770a2a5db626f
Source dataset
uspto-grants-2006_12
Patent number
US07153925B2

Reaction notes

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