alpha-Naphthyl isocyanate → N-(2-Hydroxy-4-nitrophenyl)-N′-1-naphthalenylurea

HRID 1385353Notes

Reaction equation

HRID 1385353 reaction equation
[OH:1][C:2]1[CH:8]=[C:7]([N+:9]([O-:11])=[O:10])[CH:6]=[CH:5][C:3]=1[NH2:4].[C:12]1([N:22]=[C:23]=[O:24])[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:15]=[CH:14][CH:13]=1>>[OH:1][C:2]1[CH:8]=[C:7]([N+:9]([O-:11])=[O:10])[CH:6]=[CH:5][C:3]=1[NH:4][C:23]([NH:22][C:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:15]=[CH:14][CH:13]=1)=[O:24]

Participants

3

Reactant 2

HCID 66589alpha-Naphthyl isocyanateHCID 49847212-Amino-5-Nitrophenol

Product 1

HCID 21184716N-(2-Hydroxy-4-nitrophenyl)-N′-1-naphthalenylurea

Procedure

N-(2-Hydroxy-4-nitrophenyl)-N′-(1-naphthyl)urea was prepared from 2-hydroxy 4-nitro aniline (500 mg, 3.24 mmol) and 1-naphthyl isocyanate (3.24 mmol) according to the procedure in General Method B. The product precipitated from methylene chloride and filtered. The resulting solid was titruated with 1:3 triethyl amine:methylene chloride. The filterate was concentrated in vacuo. The resulting residue was dissolved in methylene chloride and treated with 1N HCl in water. The desired product precipitated from solution and was collected by filtration (0.11 g, 10%). EI-MS m/z 324 (M+H)+

Workup

  1. customThe product precipitated from methylene chloride
  2. filtrationfiltered
  3. concentrationThe filterate was concentrated in vacuo
  4. dissolutionThe resulting residue was dissolved in methylene chloride
  5. additiontreated with 1N HCl in water
  6. customThe desired product precipitated from solution
  7. filtrationwas collected by filtration (0.11 g, 10%)

Sources & evidence

ORD record
ord-8a14fd56e72b4c87b8a6079fa2f7f55f
Source dataset
uspto-grants-2001_07
Patent number
US06262113B1

Reaction notes

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