N,O-Dimethylhydroxylamine → N'-[4-(2-naphthyloxy)phenyl]-N-methoxy-N-methylurea

HRID 1278162Notes

Reaction equation

HRID 1278162 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[O:11][C:12]1[CH:17]=[CH:16][C:15]([N:18]=[C:19]=[O:20])=[CH:14][CH:13]=1.[CH3:21][NH:22][O:23][CH3:24]>C1C=CC=CC=1>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[O:11][C:12]1[CH:17]=[CH:16][C:15]([NH:18][C:19](=[O:20])[N:22]([O:23][CH3:24])[CH3:21])=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 14232N,O-DimethylhydroxylamineHCID 127740664-(2-Naphthyloxy)phenyl isocyanate

Product 1

HCID 12893343N'-[4-(2-naphthyloxy)phenyl]-N-methoxy-N-methylureaYield 87.3%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

Thirteen grams of 4-(2-naphthyloxy)phenyl isocyanate were dissolved in 100 ml of benzene, and a solution of 4 g of N,O-dimethylhydroxylamine in 50 ml of benzene was added dropwise thereto at a temperature below 30° C. The reaction mixture was allowed to stand at room temperature for 30 minutes, and the solvent was then removed under reduced pressure. The residue was recrystallized from ethanol to obtain 14 g of N'-[4-(2-naphthyloxy)phenyl]-N-methoxy-N-methylurea as white needles. M.P., 102°-103° C.

Workup

  1. customat a temperature below 30° C
  2. customthe solvent was then removed under reduced pressure
  3. customThe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-00fa8abd9f3042a093cef9b96ed85e8a
Source dataset
uspto-grants-1981_07
Patent number
US04280835

Reaction notes

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