Phenolate → N'-{4-[(3,6-Dichloropyridin-2-yl)methoxy]phenyl}-N,N-dimethylurea

HRID 436687Notes

Reaction equation

HRID 436687 reaction equation
[Na].[CH3:2][N:3]([CH3:14])[C:4]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=1)=[O:5].C[O-].[Na+].C1([O-])C=CC=CC=1.[Cl:25][C:26]1[C:27]([CH2:33]Cl)=[N:28][C:29]([Cl:32])=[CH:30][CH:31]=1>CS(C)=O.CO>[Cl:25][C:26]1[C:27]([CH2:33][O:13][C:10]2[CH:11]=[CH:12][C:7]([NH:6][C:4](=[O:5])[N:3]([CH3:14])[CH3:2])=[CH:8][CH:9]=2)=[N:28][C:29]([Cl:32])=[CH:30][CH:31]=1

Participants

8

Reactant 5

HCID 119047PhenolateHCID 3014146Urea, N'-(4-hydroxyphenyl)-N,N-dimethyl-HCID 5360545SodiumHCID 10942334Sodium MethoxideHCID 203661743,6-Dichloro-2-(chloromethyl)pyridine

Product 1

HCID 20366179N'-{4-[(3,6-Dichloropyridin-2-yl)methoxy]phenyl}-N,N-dimethylurea

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 887MethanolSolvent

Procedure

Sodium metal (0.67 grams; 0.03 mole) was dissolved in 35 ml. of methanol and N,N-dimethyl-4-hydroxyphenyl urea (5.23 grams; 0.03 mole) was added to the sodium methoxide solution and the resulting mixture stirred until it became clear. The resulting phenolate solution was added portionwise over a period of about 90 minutes to a solution of 3,6-dichloro-2-chloromethylpyridine in 20 ml. of dimethylsulfoxide while maintaining the reaction at a temperature between from about 25° to about 50° C. The reaction mixture was then distilled to remove the methanol and the residue quenched over ice. The solid isolated by filtration was recrystallized from benzene. As a result of these operations, the desired N'-(4-((3,6-dichloro-2-pyridinyl)methoxy)phenyl)-N,N-dimethyl urea compound was recovered as a crystalline solid having a melting point of 161.5° to 162.5° C.

Workup

  1. customthe reaction at a temperature between from about 25° to about 50° C
  2. distillationThe reaction mixture was then distilled
  3. customto remove the methanol
  4. customthe residue quenched over ice
  5. customThe solid isolated by filtration
  6. customwas recrystallized from benzene
  7. customAs a result of these operations
  8. customthe desired N'-(4-((3,6-dichloro-2-pyridinyl)methoxy)phenyl)-N,N-dimethyl urea compound was recovered as a crystalline solid

Sources & evidence

ORD record
ord-ca587a706d47441782c86300624cad35
Source dataset
uspto-grants-1977_06
Patent number
US04028092

Reaction notes

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