m-Chloroperbenzoic acid → HCID 13474331, compound

HRID 977931Notes

Reaction equation

HRID 977931 reaction equation
[CH2:1]([S:8][C:9]1[CH:14]=[N:13][N:12]([CH3:15])[C:11](=[O:16])[C:10]=1[Cl:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ClC1C=CC=C(C(OO)=[O:26])C=1>ClCCl>[CH2:1]([S:8]([C:9]1[CH:14]=[N:13][N:12]([CH3:15])[C:11](=[O:16])[C:10]=1[Cl:17])=[O:26])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 28002595-benzylsulfanyl-4-chloro-2-methylpyridazin-3-one

Product 1

HCID 13474331HCID 13474331, compoundYield 77.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-20 °C

Procedure

16.0 g (60.0 millimoles) of 5-benzylthio-4-chloro-2-methylpyridazin-3(2H)-one from Method 4 were dissolved in 200 ml of dichloromethane, the solution was cooled to -20° C. and a solution of 11.4 g (66.1 millimoles) of m-chloroperbenzoic acid in dichloromethane was added dropwise. Stirring was continued for 1 hour at -10° C., and then overnight at room temperature. The reaction solution was washed three times with saturated NaHCO3 solution and once with water, dried and evaporated down, and the residue was triturated with diethyl ether and then filtered off under suction to give 13.1 g (77%) of a product of melting point 129°-131° C. (active ingredient no. 2 a).

Workup

  1. customovernight
  2. customat room temperature
  3. washThe reaction solution was washed three times with saturated NaHCO3 solution
  4. dry with materialonce with water, dried
  5. customevaporated down
  6. customthe residue was triturated with diethyl ether
  7. filtrationfiltered off under suction

Sources & evidence

ORD record
ord-4f67f1761c2145b699d4e6c29e246842
Source dataset
uspto-grants-1987_05
Patent number
US04663324

Reaction notes

Loading…