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

HRID 461586Notes

Reaction equation

HRID 461586 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

Conditions

Temperature
60 °C

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 five and one-half 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-ad8d951de7ea45ef86f0d82717b4d5ce
Source dataset
uspto-grants-1977_12
Patent number
US04063928

Reaction notes

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