Methane → N'-(4-((6-chloro-3-pyridazinyl)oxy)phenyl)-N,N-dimethylurea

HRID 268199Notes

Reaction equation

HRID 268199 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:13])[N:10]([CH3:12])[CH3:11])=[CH:4][CH:3]=1.C[O-].[Na+].[Na].[Cl:18][C:19]1[N:20]=[N:21][C:22](Cl)=[CH:23][CH:24]=1.C>C1(C)C=CC=CC=1.CCCCCC.CS(C)=O.CO>[Cl:18][C:19]1[N:20]=[N:21][C:22]([O:1][C:2]2[CH:3]=[CH:4][C:5]([NH:8][C:9](=[O:13])[N:10]([CH3:11])[CH3:12])=[CH:6][CH:7]=2)=[CH:23][CH:24]=1

Participants

10

Reactant 5

HCID 297MethaneHCID 673313,6-DichloropyridazineHCID 3014146Urea, N'-(4-hydroxyphenyl)-N,N-dimethyl-2×HCID 5360545SodiumHCID 10942334Sodium Methoxide

Product 1

HCID 13771493N'-(4-((6-chloro-3-pyridazinyl)oxy)phenyl)-N,N-dimethylurea

Reagents, catalysts & solvents 4

HCID 679Dimethyl SulfoxideSolventHCID 887MethanolSolventHCID 1140TolueneSolventHCID 8058HexaneSolvent2×

Procedure

4-Hydroxyphenyl-N,N-dimethylurea (13.5 grams; 0.075 mole) was mixed with a solution of sodium methylate (1.73 grams; 0.075 mole sodium metal in 70 milliliters (ml) of methanol) and the resulting sodium salt solution of 4-hydroxyphenyl-N,N-dimethylurea was added portionwise over a period of about one hour to a solution of 3,6-dichloropyridazine (11.2 grams; 0.075 mole) in 50 ml. of dimethylsulfoxide. During the addition and for a period of about one hour following the completion of the addition, the reaction mixture temperature was maintained between about 90° and about 95°C. Following the reaction period, the methanol was removed from the reaction mixture by evaporation and the reaction mixture extracted with methylene chloride. The methylene chloride extract was evaporated in vacuo and the waxy residue obtained dissolved in hot toluene. The resulting solution was treated with activated charcoal, cooled and hexane added thereto. The solid yellow crystalline material formed upon addition of the hexane was recovered by filtration and recrystallized from acetonitrile. As a result of these operations, the desired title compound was obtained as a white crystalline material having a melting point of 173°-174°C.

Workup

  1. additionDuring the addition
  2. additionthe completion of the addition
  3. temperaturethe reaction mixture temperature was maintained between about 90° and about 95°C
  4. customthe reaction period
  5. customthe methanol was removed from the reaction mixture by evaporation
  6. extractionthe reaction mixture extracted with methylene chloride
  7. extractionThe methylene chloride extract
  8. customwas evaporated in vacuo
  9. customthe waxy residue obtained
  10. temperaturecooled
  11. filtrationwas recovered by filtration
  12. customrecrystallized from acetonitrile
  13. customAs a result of these operations

Sources & evidence

ORD record
ord-10ba7831c8cb4948bb717c142aefc558
Source dataset
uspto-grants-1976_03
Patent number
US03947437

Reaction notes

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