Water → HCID 54408223, compound

HRID 277294

Reaction equation

HRID 277294 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[CH:6]=[O:7])#[N:2].[CH3:11][C:12]([C:14]1[CH:19]=[C:18]([C:20]#[N:21])[CH:17]=[CH:16][CH:15]=1)=O.OS(O)(=O)=O.O>C(O)(=O)C>[C:20]([C:18]1[CH:19]=[C:14]([CH:12]=[CH:11][C:6]([C:5]2[CH:8]=[CH:9][CH:10]=[C:3]([C:1]#[N:2])[CH:4]=2)=[O:7])[CH:15]=[CH:16][CH:17]=1)#[N:21]

Participants

6

Reactant 4

HCID 962WaterHCID 1118Sulfuric AcidHCID 802223-AcetylbenzonitrileHCID 90670m-Formylbenzonitrile

Product 1

HCID 54408223HCID 54408223, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

3-Cyanobenzaldehyde (3.0 g, 23.0 mmol) and 3-cyanoacetophenone (3.34 g, 23.0 mmol) in glacial acetic acid (5 mL) and concentrated H2SO4 (3.66 mL, 69 mmol) was stirred at room temperature for 72 hours. Water (200 mL) was added and the reaction filtered. The precipitate was washed with water (2×200 mL) and dried in vacuo to give 3,3′-dicyanochalcone as an off-white solid. MS (APCI) m/z 258 (M+−1, 100%). 13C NMR (50 MHz, d6-DMSO): δ111.7, 117.8, 118.0, 123.0, 129.7, 131.6, 132.1, 132.4, 133.3, 133.5, 135.3, 136.1, 137.4, 142.1, 187.3.

Workup

  1. filtrationthe reaction filtered
  2. washThe precipitate was washed with water (2×200 mL)
  3. customdried in vacuo

Sources & evidence

ORD record
ord-14ffe8cfbb58484792efb5d5d57e1733
Source dataset
uspto-grants-2002_03
Patent number
US06355683B1

Linked notes

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