Hydrogen Peroxide → 3-Methyl-2-(3-pyridylmethyl)benzo[b]thiophene-5-carboxamide

HRID 280607Notes

Reaction equation

HRID 280607 reaction equation
[OH:1]O.[CH3:3][C:4]1[C:5]2[CH:19]=[C:18]([C:20]#[N:21])[CH:17]=[CH:16][C:6]=2[S:7][C:8]=1[CH2:9][C:10]1[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=1.[OH-].[Na+].O>C(O)C>[CH3:3][C:4]1[C:5]2[CH:19]=[C:18]([C:20]([NH2:21])=[O:1])[CH:17]=[CH:16][C:6]=2[S:7][C:8]=1[CH2:9][C:10]1[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=1

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 962WaterHCID 14798Sodium HydroxideHCID 233209313-Methyl-2-(3-pyridylmethyl)benzo[b]thiophene-5-carbonitrile

Product 1

HCID 233208783-Methyl-2-(3-pyridylmethyl)benzo[b]thiophene-5-carboxamide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Hydrogen peroxide (1.6 ml of 30% w/v solution) was added to a stirred solution of 3-methyl-2-(3-pyridylmethyl)benzo[b]thiophene-5-carbonitrile (the product of Example 12(ii)) (0.30 g) in ethanol (3.5 ml) followed by 6N sodium hydroxide solution (1.6 ml). The resulting micture was heated at 50°-55° C. with stirring for 2 hours and then cooled and poured into water. The solid was filtered off, washed with water and crystallised from ethanol/water to give 3-methyl-2-(3-pyridylmethyl)benzo[b]thiophene-5-carboxamide (0.21 g), m.p. 194°-195°.

Workup

  1. temperatureThe resulting micture was heated at 50°-55° C.
  2. temperaturecooled
  3. filtrationThe solid was filtered off
  4. washwashed with water
  5. customcrystallised from ethanol/water

Sources & evidence

ORD record
ord-d4365b92f3724a0b926667b19430d3bd
Source dataset
uspto-grants-1986_05
Patent number
US04590200

Reaction notes

Loading…