P-Chloroacetophenone → HCID 86751827, compound

HRID 1941675Notes

Reaction equation

HRID 1941675 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=O)[CH3:9])=[CH:4][CH:3]=1.Cl.[NH2:12][O:13][CH2:14][CH2:15][O:16][C:17]1[CH:30]=[CH:29][C:20]([CH2:21][CH:22]2[S:26][C:25](=[O:27])[NH:24][C:23]2=[O:28])=[CH:19][CH:18]=1>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[N:12][O:13][CH2:14][CH2:15][O:16][C:17]2[CH:18]=[CH:19][C:20]([CH2:21][CH:22]3[S:26][C:25](=[O:27])[NH:24][C:23]3=[O:28])=[CH:29][CH:30]=2)[CH3:9])=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 7467P-ChloroacetophenoneHCID 218339655-(4-[2-Aminooxyethoxy)benzyl]thiazolidine-2,4-dione hydrochloride

Product 1

HCID 86751827HCID 86751827, compound

Procedure

Following a procedure similar to that described in Example 40(f), 0.18 ml of 4'-chloroacetophenone was reacted with 400 mg of 5-[4-(2-aminooxyethoxy)benzyl]-thiazolidine-2,4-dione hydrochloride [prepared as described in Example 40(e)]. The reaction mixture was then concentrated by evaporation under reduced pressure, and the resulting residue was extracted with ethyl acetate. The extract was washed with water and the solvent was removed by distillation under reduced pressure. The residue was mixed with a mixture of diethyl ether, diisopropyl ether and hexane, and the mixture was then stirred. The resulting precipitate Was collected by filtration, to give 360 mg of the title compound, melting at 118°-119° C.

Workup

  1. concentrationThe reaction mixture was then concentrated by evaporation under reduced pressure
  2. extractionthe resulting residue was extracted with ethyl acetate
  3. washThe extract was washed with water
  4. customthe solvent was removed by distillation under reduced pressure
  5. additionThe residue was mixed with a mixture of diethyl ether, diisopropyl ether and hexane
  6. filtrationThe resulting precipitate Was collected by filtration

Sources & evidence

ORD record
ord-3bab74261baa4c6f9886cde7c90c223c
Source dataset
uspto-grants-1997_12
Patent number
US05703096

Reaction notes

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