Pyridine → HCID 12893501, compound

HRID 1112572Notes

Reaction equation

HRID 1112572 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:14]=[CH:15][C:16]=1[Cl:17])[CH2:5][O:6][C:7]1[CH:13]=[CH:12][C:10]([NH2:11])=[CH:9][CH:8]=1.[CH3:18][O:19][N:20]([CH3:24])[C:21](Cl)=[O:22].N1C=CC=CC=1.[Cl-].[Na+]>C1(C)C=CC=CC=1.O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:14]=[CH:15][C:16]=1[Cl:17])[CH2:5][O:6][C:7]1[CH:13]=[CH:12][C:10]([NH:11][C:21]([N:20]([CH3:24])[O:19][CH3:18])=[O:22])=[CH:9][CH:8]=1

Participants

7

Reactant 4

HCID 1049PyridineHCID 5234Sodium ChlorideHCID 2734926N-methoxy-N-methylcarbamoyl chlorideHCID 133238854-[(3,4-Dichlorophenyl)methoxy]aniline

Product 1

HCID 12893501HCID 12893501, compoundYield 36.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

4-(3,4-Dichlorobenzyloxy)aniline (26.7 g), N-methoxy-N-methylcarbamyl chloride (13.5 g) and pyridine (8.7 g) are dissolved in toluene (200 ml), and the reaction mixture is heated under reflux for 5 hours. Water is added to the reaction mixture to dissolve the by-produced sodium chloride. The toluene layer is washed with dilute hydrochloric acid and water in that order, dried and concentrated under reduced pressure. The residual crude crystals are recrystallized from ethanol to give N-[4-(3,4-dichlorobenzyloxy)phenyl]-N'-methyl-N'-methoxyurea (Compound No. 9) (13 g) as white plates. M.P., 114° to 115° C.

Workup

  1. temperaturethe reaction mixture is heated
  2. temperatureunder reflux for 5 hours
  3. washThe toluene layer is washed with dilute hydrochloric acid and water in that order
  4. customdried
  5. concentrationconcentrated under reduced pressure
  6. customThe residual crude crystals are recrystallized from ethanol

Sources & evidence

ORD record
ord-31b86098ba204cb5be4252aa0c0853fa
Source dataset
uspto-grants-1978_10
Patent number
US04123256

Reaction notes

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