N,O-Dimethylhydroxylamine → Urea, N-methoxy-N-methyl-N'-(4-(2-(4-methylphenyl)ethoxy)phenyl)-

HRID 65819

Reaction equation

HRID 65819 reaction equation
[CH3:1][C:2]1[CH:19]=[CH:18][C:5]([CH2:6][CH2:7][O:8][C:9]2[CH:14]=[CH:13][C:12]([N:15]=[C:16]=[O:17])=[CH:11][CH:10]=2)=[CH:4][CH:3]=1.[CH3:20][NH:21][O:22][CH3:23]>C1C=CC=CC=1>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][CH2:7][O:8][C:9]2[CH:14]=[CH:13][C:12]([NH:15][C:16](=[O:17])[N:21]([O:22][CH3:23])[CH3:20])=[CH:11][CH:10]=2)=[CH:18][CH:19]=1

Participants

4

Reactant 2

HCID 14232N,O-DimethylhydroxylamineHCID 130176584-(4-Methylphenethyloxy)phenyl isocyanate

Product 1

HCID 93385Urea, N-methoxy-N-methyl-N'-(4-(2-(4-methylphenyl)ethoxy)phenyl)-Yield 108.4%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

Into a solution of 5.5 g of 4-(4-methylphenethyloxy)phenyl isocyanate in 100 ml of benzene, a solution of 2 g of N,O-dimethylhydroxylamine in 50 ml of benzene is added dropwise at 20° to 30° C. After the addition is finished, the reaction mixture is continuously stirred at the same temperature for an additional 30 minutes. Thereafter, the solvent is removed under reduced pressure, and the residue is recrystallized from ethanol to obtain 7.4 g of N'-[4-(4-methylphenethyloxy)phenyl]-N-methoxy-N-methylurea as white needles, M.P. 82°-83° C.

Workup

  1. additionAfter the addition
  2. customThereafter, the solvent is removed under reduced pressure
  3. customthe residue is recrystallized from ethanol

Sources & evidence

ORD record
ord-a066c1df694a417684942b3232fa807c
Source dataset
uspto-grants-1978_12
Patent number
US04129436

Linked notes

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