Dichloromethane → HCID 18323823, compound

HRID 1872039Notes

Reaction equation

HRID 1872039 reaction equation
[CH3:1][S:2]([C:4]1[CH:9]=[C:8]([CH:10]([CH3:12])[CH3:11])[CH:7]=[CH:6][C:5]=1[N:13]([CH2:22][CH3:23])[C:14]1[N:19]=[C:18]([CH3:20])[CH:17]=[C:16]([CH3:21])[N:15]=1)=[O:3].C(Cl)Cl.[O-:27][Mn](=O)(=O)=O.[K+]>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.O>[CH3:1][S:2]([C:4]1[CH:9]=[C:8]([CH:10]([CH3:12])[CH3:11])[CH:7]=[CH:6][C:5]=1[N:13]([CH2:22][CH3:23])[C:14]1[N:19]=[C:18]([CH3:20])[CH:17]=[C:16]([CH3:21])[N:15]=1)(=[O:27])=[O:3]

Participants

6

Reactant 3

HCID 6344DichloromethaneHCID 516875Potassium PermanganateHCID 18323818HCID 18323818, compound

Product 1

HCID 18323823HCID 18323823, compoundYield 81.5%

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 962WaterSolvent

Procedure

The sulfoxide of Example 37, (100 mg, 0.3 mmoles) was stirred at 4 mL of CH2Cl2 and 8 mL water with 20 mg (0.09 mmole) of benzyltriethylammonium chloride and 94.5 mg (0.6 mmole) KMnO4 at 25° C. for 16 h. The mixture was partitioned between 60 mL EtOAc and 40 mL water and the EtOAc was washed with water, brine, dried and stripped in vacuo. The residue was purified by silica gel chromatography using 25% EtOAc/hexanes to give 85 mg product (81% yield); mp 174-175.3° C. Elemental analysis for C18H25N3O2S: Theory C: 62.22, H: 7.25, N: 12.09, S: 9.23, Found: C: 62.13, H: 7.28 , N: 11.93, S: 9.12.

Workup

  1. customThe mixture was partitioned between 60 mL EtOAc and 40 mL water
  2. washthe EtOAc was washed with water, brine
  3. customdried
  4. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-6a4845dfd44d455f956ebf448c70fd88
Source dataset
uspto-grants-2000_08
Patent number
US06107301

Reaction notes

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