Ammonium Chloride → 3-Cyano-5-[6-(N,N-di-ethenylamino)benzo[b]furanylmethylene]-4-phenyl-2-furanone

HRID 1709314Notes

Reaction equation

[CH2:1]([N:3]([C:6]1[CH:7]=[CH:8][C:9]2[CH:13]=[C:12]([CH:14]=O)[O:11][C:10]=2[CH:16]=1)[CH2:4][CH3:5])[CH3:2].[C:17]([CH:19]1[C:23]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[CH:22][O:21][C:20]1=[O:30])#[N:18].[NH4+].[Cl-]>N1C=CC=CC=1>[C:17]([C:19]1[C:20](=[O:30])[O:21][C:22](=[CH:14][C:12]2[O:11][C:10]3[CH:16]=[C:6]([N:3]([CH:1]=[CH2:2])[CH:4]=[CH2:5])[CH:7]=[CH:8][C:9]=3[CH:13]=2)[C:23]=1[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)#[N:18]

Participants

Conditions

Temperature: 80 °C

Procedure

To 5 mL of pyridine in a 15 mL round bottom flask was added 217 mg (1 mmol) of the compound of Example 2 and 172 mg (1 mmol) of 3-cyano-4-phenyl-2-furanone. The solution was heated at 80° C. for one hour, cooled and poured into 20 mL dilute NH4Cl. The resulting mixture was extracted 2X with 20 mL 3:2 hexanes Et2O and the combined organic extracts were washed once with 10 mL of water, The organic phase was dried (MgSO4) and the solvent removed by rotary evaporation. The resulting solid was purified by flash chromatography (7:2 cyclohexane/EtOA; SiO2, 1×12") to yield 292 mg of dye. Anal. calcd. for C24H20N2O3 : C, 74.2; H, 5.4; N, 7.5. Found: C, 74.0; H, 5.2; N, 6.9.

Workup

temperaturecooled
extractionThe resulting mixture was extracted 2X with 20 mL 3:2 hexanes Et2O
washthe combined organic extracts were washed once with 10 mL of water
dry with materialThe organic phase was dried (MgSO4)
customthe solvent removed by rotary evaporation
customThe resulting solid was purified by flash chromatography (7:2 cyclohexane/EtOA; SiO2, 1×12")
customto yield 292 mg of dye

Sources & evidence

ORD record: ord-f6214208cbcb43348150f73e30c23ed8
Source dataset: uspto-grants-1990_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04948895

Reaction notes

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