Water → 3,3'-Dicyanochalcone

HRID 1987714Notes

Reaction equation

HRID 1987714 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 544082233,3'-Dicyanochalcone

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): δ 111.7, 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-e889d83efe16491e91002871b8bd0ce7
Source dataset
uspto-grants-2009_06
Patent number
US07553809B2

Reaction notes

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