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

HRID 1112570Notes

Reaction equation

HRID 1112570 reaction equation
[F:1][C:2]1[CH:18]=[CH:17][CH:16]=[CH:15][C:3]=1[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([N:12]=[C:13]=[O:14])=[CH:8][CH:7]=1.[CH3:19][NH:20][O:21][CH3:22]>C1C=CC=CC=1>[F:1][C:2]1[CH:18]=[CH:17][CH:16]=[CH:15][C:3]=1[CH2:4][O:5][C:6]1[CH:7]=[CH:8][C:9]([NH:12][C:13]([N:20]([CH3:19])[O:21][CH3:22])=[O:14])=[CH:10][CH:11]=1

Participants

4

Reactant 2

HCID 14232N,O-DimethylhydroxylamineHCID 22762251HCID 22762251, compound

Product 1

HCID 12893493N'-{4-[(2-Fluorophenyl)methoxy]phenyl}-N-methoxy-N-methylureaYield 59.2%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

To a solution of 4-(2-fluorobenzyloxy)phenyl isocyanate (24.3 g) in benzene (150 ml), a solution of N,O-dimethylhydroxylamine (20 g) in benzene (100 ml) is added dropwise at 20° to 30° C., and the resulting mixture is stirred at the same temperature for 30 minutes. The reaction mixture is concentrated in vacuo, and the residual crude crystals are recrystallized from ethanol to give N-[4-(2-fluorobenzyloxy)phenyl]-N'-methyl-N'-methoxyurea (Compound No. 1) (18 g) as white scales. M.P., 99° to 100° C.

Workup

  1. concentrationThe reaction mixture is concentrated in vacuo
  2. customthe residual crude crystals are recrystallized from ethanol

Sources & evidence

ORD record
ord-3cb20502903140ee8aefd57c2f780501
Source dataset
uspto-grants-1978_10
Patent number
US04123256

Reaction notes

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