Hydrogen Peroxide → HCID 23346242, compound

HRID 1856203Notes

Reaction equation

HRID 1856203 reaction equation
Cl.[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([S:9][C:10]2[CH2:11][CH2:12][N:13]([CH2:16][CH2:17][CH2:18][C:19]([C:21]3[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=3)=[O:20])[CH2:14][CH:15]=2)=[CH:5][CH:4]=1.OO.S(=O)(O)[O-:31].[Na+].[C:35]([CH:38]([CH:40]([C:42]([O-:44])=[O:43])[OH:41])[OH:39])([O-:37])=[O:36]>C(O)(=O)C.CCOCC>[OH:39][CH:38]([CH:40]([OH:41])[C:42]([OH:44])=[O:43])[C:35]([OH:37])=[O:36].[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([C:10]2[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][CH2:18][C:19]([C:21]3[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=3)=[O:20])[CH2:12][CH:11]=2)=[O:31])=[CH:5][CH:4]=1

Participants

7

Reactant 4

HCID 784Hydrogen PeroxideHCID 38061142,3-DihydroxybutanedioateHCID 23346248HCID 23346248, compoundHCID 23665763Sodium Bisulfite

Product 1

HCID 23346242HCID 23346242, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent2×HCID 3283Diethyl EtherSolvent

Procedure

A solution of 7.5 g of 4-{4-[(4-chlorophenyl)thio]-1,2,3,6-tetrahydro-1-pyridinyl}-1-(4-fluorophenyl)-1-butanone hydrochloride, 1.8 g of 30% hydrogen peroxide in 100 ml of acetic acid is allowed to stand at room temperature for 6 days. A small quantity of sodium bisulfite is added after which the acetic acid is removed in vacuo. The residue is neutralized with dilute sodium carbonate solution, and the product extracted into chloroform. The solvent is evaporated to give an oil. The tartrate salt is generated in ether and triturated with boiling ethyl acetate to yield a white powder, m.p. 159°-160° C.

Workup

  1. customis removed in vacuo
  2. extractionthe product extracted into chloroform
  3. customThe solvent is evaporated
  4. customto give an oil
  5. customtriturated with boiling ethyl acetate
  6. customto yield a white powder, m.p. 159°-160° C.

Sources & evidence

ORD record
ord-598f0192d8724ad69b210180a0e92e59
Source dataset
uspto-grants-1980_08
Patent number
US04218455

Reaction notes

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