Dimethylformamide → HCID 23039520, compound

HRID 2166332Notes

Reaction equation

HRID 2166332 reaction equation
CN(C)C=O.[Cl:6][C:7]1[C:8](=[O:18])[N:9]([CH2:14][CH2:15][CH2:16][OH:17])[N:10]=[CH:11][C:12]=1[OH:13].[Cl:19][C:20]1[CH:27]=[CH:26][C:23]([CH2:24]Cl)=[CH:22][CH:21]=1.C(=O)([O-])[O-].[K+].[K+]>O>[Cl:6][C:7]1[C:8](=[O:18])[N:9]([CH2:14][CH2:15][CH2:16][OH:17])[N:10]=[CH:11][C:12]=1[O:13][CH2:24][C:23]1[CH:26]=[CH:27][C:20]([Cl:19])=[CH:21][CH:22]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 77231-Chloro-4-(chloromethyl)benzeneHCID 11430Potassium CarbonateHCID 54731250HCID 54731250, compound

Product 1

HCID 23039520HCID 23039520, compoundYield 74.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 150 ml of N,N-dimethylformamide were added 10.2 g of 4-chloro-5-hydroxy-2-(3'-hydroxypropyl)-3(2H)-pyridazinone (0.05 mol), 8.4 g of 4-chlorobenzyl chloride (0.052 mol) and 10.4 g of anhydrous potassium carbonate (0.075 mol) and heated for about 3 hours at 100° C. to 120° C. After reaction, the mixture solution was poured into water and extracted with ethyl acetate. The resulting solution was washed with water and then with aqueous solution of 5% sodium hydroxide and further with saturated saline. The solution was dried over anhydrous sodium sulfate and the solvent was distilled off under reduced pressure. The solid product thus obtained was washed with n-hexane and dried to obtain 12.3 g of 4-chloro-5-(4'-chlorobenzyloxy)-2-(3'-hydroxypropyl)-3(2H)-pyridazinone.

Workup

  1. temperatureheated for about 3 hours at 100° C. to 120° C
  2. customAfter reaction
  3. extractionextracted with ethyl acetate
  4. washThe resulting solution was washed with water
  5. dry with materialThe solution was dried over anhydrous sodium sulfate
  6. distillationthe solvent was distilled off under reduced pressure
  7. customThe solid product thus obtained
  8. washwas washed with n-hexane
  9. customdried

Sources & evidence

ORD record
ord-dfce0268a6a24851a57bcc917af6cb13
Source dataset
uspto-grants-1990_07
Patent number
US04945091

Reaction notes

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