Chloroform → HCID 14577239, compound

HRID 2166333Notes

Reaction equation

HRID 2166333 reaction equation
C(Cl)(Cl)Cl.[Cl:5][C:6]1[C:7](=[O:25])[N:8]([CH2:21][CH2:22][CH2:23]O)[N:9]=[CH:10][C:11]=1[O:12][CH2:13][C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=1.S(Br)([Br:28])=O>O>[Br:28][CH2:23][CH2:22][CH2:21][N:8]1[C:7](=[O:25])[C:6]([Cl:5])=[C:11]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=2)[CH:10]=[N:9]1

Participants

5

Reactant 3

HCID 6212ChloroformHCID 68176Thionyl bromideHCID 23039520HCID 23039520, compound

Product 1

HCID 14577239HCID 14577239, compoundYield 44.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 170 ml of chloroform were added 9.9 g of 4-chloro-5-(4'-chlorobenzyloxy)-2-(3'-hydroxypropyl)-3(2H)-pyridazinone (0.03 mol) and slowly added 9.4 g of thionyl bromide (0.045 mol) under stirring for about 2 hours at -5° to 5° C. After reaction, the resulting solution was added little by little with water and the chloroform layer was separated. The layer was washed with water and then with aqueous solution of 5% sodium hydrogen carbonate, and further washed with saturated saline and dried over anhydrous sodium sulfate and freed of solvent by distillation under reduced pressure. The solid product thus obtained was recrystallized from a mixed solvent of n-hexane-benzene to give 5.2 g of 2-(3'-bromopropyl)-4-chloro-5-(4'-chlorobenzyloxy)-3(2H)-pyridazinone.

Workup

  1. customAfter reaction
  2. customthe chloroform layer was separated
  3. washThe layer was washed with water
  4. washwith aqueous solution of 5% sodium hydrogen carbonate, and further washed with saturated saline
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationfreed of solvent by distillation under reduced pressure
  7. customThe solid product thus obtained
  8. customwas recrystallized from a mixed solvent of n-hexane-benzene

Sources & evidence

ORD record
ord-f1e41692634c44f6bf32bd2dbb7a4b55
Source dataset
uspto-grants-1990_07
Patent number
US04945091

Reaction notes

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