Pyridine → N'-{4-[(4-Fluorophenyl)methoxy]phenyl}-N-methoxy-N-methylurea

HRID 1112571Notes

Reaction equation

HRID 1112571 reaction equation
[F:1][C:2]1[CH:16]=[CH:15][C:5]([CH2:6][O:7][C:8]2[CH:14]=[CH:13][C:11]([NH2:12])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[CH3:17][N:18]([O:22][CH3:23])[C:19](Cl)=[O:20].N1C=CC=CC=1.Cl.N1C=CC=CC=1>C1C=CC=CC=1.O>[F:1][C:2]1[CH:16]=[CH:15][C:5]([CH2:6][O:7][C:8]2[CH:14]=[CH:13][C:11]([NH:12][C:19]([N:18]([CH3:17])[O:22][CH3:23])=[O:20])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 1049PyridineHCID 2734926N-methoxy-N-methylcarbamoyl chlorideHCID 64860214-(4-Fluoro-benzyloxy)-phenylamineHCID 10176127Pyridinium chloride

Product 1

HCID 12893495N'-{4-[(4-Fluorophenyl)methoxy]phenyl}-N-methoxy-N-methylurea

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 962WaterSolvent

Procedure

To a solution of 4-(4-fluorobenzyloxy)aniline (21.7 g) in benzene (150 ml), N-methyl-N-methoxycarbamyl chloride (14.7 g) and pyridine (11.8 g) are added thereto, and the reaction mixture is heated under reflux for 17 hours. The reaction mixture is cooled to room temperature, and water is added thereto to dissolve the by-produced pyridine hydrochloride. After separation of the aqueous layer, the benzene layer is washed with dilute hydrochloric acid and water in that order, dried and concentrated in vacuo to give N-[4-(4-fluorobenzyloxy)phenyl]-N'-methyl-N'-methoxyurea (Compound No. 3) (11 g) as white plates. M.P., 123° to 124.5° C.

Workup

  1. temperaturethe reaction mixture is heated
  2. temperatureunder reflux for 17 hours
  3. customAfter separation of the aqueous layer
  4. washthe benzene layer is washed with dilute hydrochloric acid and water in that order
  5. customdried
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4782236e1e1947718c338823c5e3393d
Source dataset
uspto-grants-1978_10
Patent number
US04123256

Reaction notes

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