Sodium Hydroxide → N'-(4-((6-chloro-2-pyridinyl)oxy)phenyl)-N,N-dimethyl urea-1-oxide

HRID 437281Notes

Reaction equation

HRID 437281 reaction equation
[OH-:1].[Na+].[OH:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11](=[O:15])[N:12]([CH3:14])[CH3:13])=[CH:6][CH:5]=1.[Cl:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19](Cl)[N+:18]=1[O-]>CS(C)=O>[Cl:16][C:17]1[N:18]=[C:19]([O:3][C:4]2[CH:5]=[CH:6][C:7]([NH:10][C:11](=[O:15])[N+:12]([O-:1])([CH3:13])[CH3:14])=[CH:8][CH:9]=2)[CH:20]=[CH:21][CH:22]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 8176732,6-Dichloropyridine N-OxideHCID 3014146Urea, N'-(4-hydroxyphenyl)-N,N-dimethyl-

Product 1

HCID 21391435N'-(4-((6-chloro-2-pyridinyl)oxy)phenyl)-N,N-dimethyl urea-1-oxide

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Dry powdered sodium hydroxide (2.44 grams; 0.061 mole) was dissolved in 110 ml. of warm dimethylsulfoxide and N'-(4-hydroxyphenyl)-N,N-dimethyl urea (11.0 grams; 0.061 mole) and 2,6-dichloropyridine-N-oxide added thereto. The reaction mixture was stirred at a temperature of about 60° C. for a period of 51/2 hours. After this period, about three-fourths of the solvent carrier was removed by vacuum distillation and the residual oil thus obtained poured into ice water. The aqueous mixture was extracted with three 250 ml. portions of warm methylene chloride and the extracts combined. Evaporation of the solvent from the extract left a brown, syrupy residue which was washed with cold water and then with dry benzene to give the desired N'-(4-((6-chloro-2-pyridinyl)oxy)phenyl)-N,N-dimethyl urea-1-oxide compound as a crystalline solid melting at 190°-191° C. and having carbon, hydrogen, nitrogen and chlorine contents of 53.83, 4.63, 13.25 and 12.78 percent, respectively, as compared with contents of 54.64, 4.58, 13.65 and 11.52 percent, respectively, calculated for the named structure.

Workup

  1. dissolutionwas dissolved in 110 ml
  2. waitAfter this period
  3. customabout three-fourths of the solvent carrier was removed by vacuum distillation
  4. customthe residual oil thus obtained
  5. extractionThe aqueous mixture was extracted with three 250 ml
  6. customEvaporation of the solvent from the extract
  7. waitleft a brown, syrupy residue which
  8. washwas washed with cold water

Sources & evidence

ORD record
ord-21c90588a5ce41d09c31c110cd064835
Source dataset
uspto-grants-1977_06
Patent number
US04030910

Reaction notes

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