Dimethyl Sulfoxide → HCID 58917756, compound

HRID 415701Notes

Reaction equation

HRID 415701 reaction equation
[CH:1]([C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH2:12][C:13]1[CH:20]=[CH:19][C:16]([C:17]#[N:18])=[CH:15][CH:14]=1)[CH:7]=[CH:6]2)=[O:2].C(=O)([O-])[O-:22].[K+].[K+].CS(C)=O.OO>O>[CH:1]([C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH2:12][C:13]1[CH:20]=[CH:19][C:16]([C:17]([NH2:18])=[O:22])=[CH:15][CH:14]=1)[CH:7]=[CH:6]2)=[O:2]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 784Hydrogen PeroxideHCID 11430Potassium CarbonateHCID 58917751HCID 58917751, compound

Product 1

HCID 58917756HCID 58917756, compoundYield 169.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Mix 4-(5-Formyl-indol-1-ylmethyl)-benzonitrile (0.73 g, 2.8 mmol), potassium carbonate (0.19 g, 1.4 mmol), and dimethylsulfoxide (14 mL) in a flask. Cool 10 minutes in an ice bath and add hydrogen peroxide (0.95 mL, 30% wt in water) dropwise. Remove ice bath and stir at rt for 4 hrs. Pour into water (30 mL). After trituration, filter the solid formed and dry on a vacuum pump to obtain the product as a white solid (0.66 g, 88%). 1H NMR (DMSO-d6) 9.95 (s, 1H), 8.17 (s, 1H), 7.89 (bs, 1H), 7.78 (d, J=8.1 Hz, 2H), 7.69 (d, J=3.1 Hz, 1H), 7.63-7.60 (m, 2H), 7.32 (bs, 1H), 7.23 (d, J=8.1 Hz, 2H), 6.73 (d, J=3.1 Hz, 1H), 5.54 (s, 2H).

Workup

  1. temperatureCool 10 minutes in an ice bath
  2. filtrationAfter trituration, filter the solid
  3. customformed
  4. customdry on a vacuum pump

Sources & evidence

ORD record
ord-3a8ab03446044f65a2d9d18735dec4e2
Source dataset
uspto-grants-2012_01
Patent number
US08088800B2

Reaction notes

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