Dimethylamine → N'-(4-Hydroxy-3-nitrophenyl)-N,N-dimethylurea

HRID 2164866Notes

Reaction equation

HRID 2164866 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]=[C:9]=[O:10])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12].NC1C=CC(O)=C([N+]([O-])=O)C=1.C(Cl)(Cl)=O.[CH3:29][NH:30][CH3:31]>C1(C)C=CC=CC=1>[OH:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([N:30]([CH3:31])[CH3:29])=[O:10])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12]

Participants

6

Reactant 4

HCID 674DimethylamineHCID 6371PhosgeneHCID 34174194-Amino-2-NitrophenolHCID 12483477HCID 12483477, compound

Product 1

HCID 20403414N'-(4-Hydroxy-3-nitrophenyl)-N,N-dimethylurea

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

4-Hydroxy-3-nitrophenylisocyanate (15.5 g), prepared as described by H. Ulrich et al., loc. cit., from 4-amino-2-nitrophenol and phosgene, is added to 100 g of a solution of 29% by weight of dimethylamine in toluene, and the mixture is stirred at room temperature for 2 hours. Evaporation under reduced pressure leaves a residue on recrystallization from water gives N-(4-hydroxy-3-nitrophenyl)-N',N'-dimethylurea, m.pt. 142° C.

Workup

  1. customEvaporation under reduced pressure
  2. customleaves a residue
  3. customon recrystallization from water

Sources & evidence

ORD record
ord-4e526c29653c478bb2d3759192241978
Source dataset
uspto-grants-1985_03
Patent number
US04507445

Reaction notes

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