Methanol → HCID 501225, compound

HRID 2300990Notes

Reaction equation

HRID 2300990 reaction equation
[Cl:1][C:2]1[C:3]([S:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[N+:4]([O-:8])[CH:5]=[CH:6][CH:7]=1.C[OH:18]>>[Cl:1][C:2]1[C:3]([S:9]([CH2:10][C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)=[O:18])=[N+:4]([O-:8])[CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 887MethanolHCID 501226HCID 501226, compound

Product 1

HCID 501225HCID 501225, compound

Procedure

To 4.7 g of the starting sulfide (Sec Example 24 above) dissolved in 25 ml of methanol were added a pinch of Na2WO4 followed by 1.5 g of 50% aqueous hydrogren peroxide. The mixture was stirred at room temperature for four hours, filtered, and the solid was washed with NaHSO3 solution, followed by water. The dried solid 2.2 g, melting point of 119-122° C., gave an NMR which indicated mostly the desired sulfoxide but some contamination by the sulfone and sulfide. A second crop of 1.1 g, melting point 118-123° C., was also obtained. Attempts to recrystallize from toluene and from ethyl acetate gave material still contaminated by sulfone, so the mixture was finally separated by preparative HPLC and then recrystallized from ethyl acetate, having a melting point of 124-126° C. The elemental analysis for C,N&N, the infrared spectrum, and the NMR spectrum were all consistent with the proposed structure.

Workup

  1. filtrationfiltered
  2. washthe solid was washed with NaHSO3 solution

Sources & evidence

ORD record
ord-4a8a9350d0fe4be18bf524a9746c931d
Source dataset
uspto-grants-2002_12
Patent number
US06498254B1

Reaction notes

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