5-[5-(4-Chloro-phenyl)-2-oxo-6H-[1,3,4]oxadiazin-3-ylmethyl]-3-methyl-sulphanyl-1,3-dihydro-indol-2-one → 5-[5-(4-Chloro-phenyl)-2-oxo-6H-[1,3,4]oxadiazin-3-ylmethyl]-1,3-dihydro-indol-2-one

HRID 241744Notes

Reaction equation

HRID 241744 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH2:13][O:12][C:11](=[O:14])[N:10]([CH2:15][C:16]3[CH:17]=[C:18]4[C:22](=[CH:23][CH:24]=3)[N:21](S)[C:20](=[O:26])[CH:19]4C)[N:9]=2)=[CH:4][CH:3]=1>C(O)(=O)C.[Zn]>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH2:13][O:12][C:11](=[O:14])[N:10]([CH2:15][C:16]3[CH:17]=[C:18]4[C:22](=[CH:23][CH:24]=3)[NH:21][C:20](=[O:26])[CH2:19]4)[N:9]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 866624325-[5-(4-Chloro-phenyl)-2-oxo-6H-[1,3,4]oxadiazin-3-ylmethyl]-3-methyl-sulphanyl-1,3-dihydro-indol-2-one

Product 1

HCID 666361855-[5-(4-Chloro-phenyl)-2-oxo-6H-[1,3,4]oxadiazin-3-ylmethyl]-1,3-dihydro-indol-2-one

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

Powdered Zn (157.3 mmoles) is added to a solution of the compound obtained in Step F (15.73 mmoles) in glacial acetic acid (150 ml). The reaction mixture is stirred for 6 hours and then filtered. The filtrate is evaporated to dryness and then taken up in water (200 ml) and DCM (400 ml). The phases are separated and the aqueous phase is extracted with DCM; the organic phases are combined. The organic phase obtained is washed with water and then with saturated NaCl solution, dried over sodium sulphate, filtered and evaporated to dryness. The residue obtained is recrystallised from ethanol to yield the title product.

Workup

  1. filtrationfiltered
  2. customThe filtrate is evaporated to dryness
  3. customThe phases are separated
  4. extractionthe aqueous phase is extracted with DCM
  5. customThe organic phase obtained
  6. washis washed with water
  7. dry with materialwith saturated NaCl solution, dried over sodium sulphate
  8. filtrationfiltered
  9. customevaporated to dryness
  10. customThe residue obtained
  11. customis recrystallised from ethanol

Sources & evidence

ORD record
ord-08d03176274c4ad49c0a8c109cd5e80c
Source dataset
uspto-grants-2014_02
Patent number
US08653073B2

Reaction notes

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