HCID 19349406, compound → HCID 19349411, compound

HRID 2107771Notes

Reaction equation

HRID 2107771 reaction equation
[CH3:1][C:2]([C:6]1[CH:11]=[C:10]([CH2:12][N:13]2[CH:17]=[N:16][CH:15]=[N:14]2)[CH:9]=[C:8]([CH2:18][S:19][CH3:20])[CH:7]=1)([CH3:5])[C:3]#[N:4].I([O-])(=O)(=O)=[O:22].[Na+]>CO.O1CCCC1.O>[CH3:5][C:2]([C:6]1[CH:11]=[C:10]([CH2:12][N:13]2[CH:17]=[N:16][CH:15]=[N:14]2)[CH:9]=[C:8]([CH2:18][S:19]([CH3:20])=[O:22])[CH:7]=1)([CH3:1])[C:3]#[N:4]

Participants

6

Reactant 2

HCID 19349406HCID 19349406, compoundHCID 23667635Sodium periodate

Product 1

HCID 19349411HCID 19349411, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

A solution of the product of Example 30 (0.16 g) in methanol (0.5 ml) and tetrahydrofuran (5 ml) was stirred while a solution of sodium periodate (0.15 g) in water (0.5 ml) was added, and was then stirred at room temperature for a further 18 h. Water (5 ml) was added and the mixture was extracted six times with dichloromethane. The extracts were combined, dried and evaporated to dryness, and the residue was purified by flash column chromatography, eluting with methanol:ethyl acetate (1:9 by volume) to give 2-methyl-2-[3-methylsulphinylmethyl-5-(1H-1,2,4-triazol-1-ylmethyl)phenyl]-propiononitrile. Nmr in deuteriochloroform; δ 8.16(1H,s), 8.0(1H,s), 7.38(1H,m), 7.27(1H,m), 7.15(1H,m), 5.4(2H,s), 3.98(1H,d), 3.88(1H,d), 2.5(3H,s), 1.72(6H,s).

Workup

  1. additionwas added
  2. extractionthe mixture was extracted six times with dichloromethane
  3. customdried
  4. customevaporated to dryness
  5. customthe residue was purified by flash column chromatography
  6. washeluting with methanol:ethyl acetate (1:9 by volume)

Sources & evidence

ORD record
ord-614a810db5c248f8864d32df30b8d50e
Source dataset
uspto-grants-1990_06
Patent number
US04935437

Reaction notes

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