Acetic Acid → HCID 86711622, compound

HRID 527352Notes

Reaction equation

HRID 527352 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:17]=[CH:18][C:19]=1[S:20]([CH3:24])=[N:21][C:22]#[N:23])[CH2:5][N:6]1[C:14](=[O:15])[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]1=[O:16].C(O)(=[O:27])C.[Mn]([O-])(=O)(=O)=O.[K+].[O-]S([O-])(=S)=O.[Na+].[Na+]>O.C(#N)C>[F:1][C:2]1[CH:3]=[C:4]([CH:17]=[CH:18][C:19]=1[S:20]([CH3:24])(=[N:21][C:22]#[N:23])=[O:27])[CH2:5][N:6]1[C:7](=[O:16])[C:8]2[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:14]1=[O:15]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 24477Sodium ThiosulfateHCID 516875Potassium PermanganateHCID 86711621HCID 86711621, compound

Product 1

HCID 86711622HCID 86711622, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

2-(3-Fluoro-4-(N-cyano-S-methylsulfinimidoyl)-benzyl)-isoindole-1,3-dione (preparation 15b, 1.60 g, 4.22 mmol) and acetic acid (0.25 g, 4.22 mmol) are added to a solution of potassium permanganate (670 mg, 4.22 mmol) in a mixture of water (8 mL) and acetonitrile (9.6 ml). The mixture is stirred over night, and saturated aqueous Na2S2O3 solution is added. The mixture is extracted with ethyl acetate and the organic layer is dried over Na2SO4. The residue is directly used in the next step without further purification. Yield: 1.34 g (80% of theory); ESI mass spectrum: [M+H]+=358; r.t. HPLC: 0.73 min (5-95AB).

Workup

  1. extractionThe mixture is extracted with ethyl acetate
  2. dry with materialthe organic layer is dried over Na2SO4
  3. customThe residue is directly used in the next step without further purification
  4. customr.t
  5. custom0.73 min (5-95AB)

Sources & evidence

ORD record
ord-53b1dd1fc2494f7ead2fe17dd0b45823
Source dataset
uspto-grants-2016_05
Patent number
US09346794B1

Reaction notes

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