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Sodium periodate → 2-[2,4-dichloro-5-(2-propynyloxy)phenyl]-2,4-dihydro-5-(3-oxo-propyl)-3H-1,2,4-triazol-3-one

HRID 1965
Notes
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Reaction equation

HRID 1965 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([O:9][CH2:10][C:11]#[CH:12])=[CH:4][C:3]=1[N:13]1[C:17](=[O:18])[NH:16][C:15]([CH2:19][CH2:20][CH:21]=C)=[N:14]1.I([O-])(=O)(=O)=[O:24].[Na+]>O1CCCC1.O.[Os](=O)(=O)(=O)=O>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([O:9][CH2:10][C:11]#[CH:12])=[CH:4][C:3]=1[N:13]1[C:17](=[O:18])[NH:16][C:15]([CH2:19][CH2:20][CH:21]=[O:24])=[N:14]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 2

HCID 23667635Sodium periodateHCID 1359741252-[2,4-dichloro-5-(2-propynyloxy)phenyl]-2,4-dihydro-5-(3-butenyl)-3H-1,2,4-triazol-3-one

Product 1

HCID 1360931112-[2,4-dichloro-5-(2-propynyloxy)phenyl]-2,4-dihydro-5-(3-oxo-propyl)-3H-1,2,4-triazol-3-oneYield 92.2%

Reagents, catalysts & solvents 3

HCID 30318Osmium TetroxideCatalyst
HCID 962
Water
Solvent
2×
HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 500 mg (1.48 mmol) of 2-[2,4-dichloro-5-(2-propynyloxy)phenyl]-2,4-dihydro-5-(3-butenyl)-3H-1,2,4-triazol-3-one in a mixture of 10 mL of tetrahydrofuran and 10 mL of water was added 696 mg (3.25 mmol) of sodium periodate and 167 mL of 0.18M aqueous solution of osmium tetroxide at room temperature. The mixture was stirred at the room temperature for 2h, and then diluted with water and extracted with ethyl acetate. The organic layer was dried (MgSO4) and concentrated in vacuo. The crude product was purified by flash chromatography over silica gel, eluting with a 96:4 v:v mixture of dichloromethane and methanol to give 464 mg of the title product of Step 1 as a white foam. 1H NMR (CDCI3, 400 MHz) δ 11.5 (broad s,1H), 9.8 (s,1H), 7.55 (s,1H), 7.2 (s,1H), 4.8 (s,2H), 2.9 (m,4H).

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic layer was dried (MgSO4)
  3. concentrationconcentrated in vacuo
  4. customThe crude product was purified by flash chromatography over silica gel
  5. washeluting with a 96:4 v
  6. additionv mixture of dichloromethane and methanol

Sources & evidence

ORD record
ord-64c534178a4a4c3f822722a59b57a089
Source dataset
uspto-grants-1998_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05728651

Reaction notes

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