Nitromethane → 2-(2-Nitroethenyl)-1-benzothiophene

HRID 1843836Notes

Reaction equation

HRID 1843836 reaction equation
[S:1]1[C:5]([CH:6]=O)=[CH:4][C:3]2[CH:8]=[CH:9][CH:10]=[CH:11][C:2]1=2.[N+:12]([CH3:15])([O-:14])=[O:13].[OH-].[Na+]>C(O)C>[N+:12]([CH:15]=[CH:6][C:5]1[S:1][C:2]2[CH:11]=[CH:10][CH:9]=[CH:8][C:3]=2[CH:4]=1)([O-:14])=[O:13]

Participants

5

Reactant 3

HCID 6375NitromethaneHCID 14798Sodium HydroxideHCID 7365001-Benzothiophene-2-carbaldehyde

Product 1

HCID 668016392-(2-Nitroethenyl)-1-benzothiopheneYield 85.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

Using an analogous reaction procedure and workup as described in Example 1, step 1, benzo[b]thiophene-2-carbaldehyde (2.1 g, 0.012 mol) in ethanol (100 mL) was reacted with nitro methane (0.7 mL, 0.012 mol) and 10N NaOH (0.51 g, 0.012 mol). The resulting mixture was stirred at 0° C. for 1 hr to afford 2.1 g of the product (84% yield).

Workup

  1. customan analogous reaction procedure

Sources & evidence

ORD record
ord-900cfe39f4c34345b810a417df4b192b
Source dataset
uspto-grants-2015_02
Patent number
US08946260B2

Reaction notes

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