Dichloromethane → HCID 86626449, compound

HRID 736858Notes

Reaction equation

HRID 736858 reaction equation
[CH:1]([NH:3]/[C:4](/[C:14](/[NH:24][CH:25]=O)=[CH:15]\[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[O:22][CH3:23])=[CH:5]/[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[O:12][CH3:13])=O.ClCCl.P(Cl)(Cl)(Cl)=O.C(=O)([O-])O.[Na+]>C(Cl)(Cl)Cl.N1C=CC=CC=1.C(OCC)(=O)C>[N+:3](/[C:4](/[C:14](/[N+:24]#[C-:25])=[CH:15]\[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[O:22][CH3:23])=[CH:5]/[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[O:12][CH3:13])#[C-:1]

Participants

8

Reactant 4

HCID 6344DichloromethaneHCID 24813Phosphorus oxychlorideHCID 516892Sodium BicarbonateHCID 86626450HCID 86626450, compound

Product 1

HCID 86626449HCID 86626449, compoundYield 72.4%

Reagents, catalysts & solvents 3

HCID 1049PyridineSolventHCID 6212ChloroformSolventHCID 8857Ethyl AcetateSolvent

Procedure

1,1′-[(1E,3E)-2,3-diformylamino-1,3-butadiene-1,4-diyl]bis[methoxybenzene] (3.4 mg, 0.0096 mmol) prepared in Reference Synthetic Example 6 was suspended in chloroform (100 μl) and pyridine (100 μl), and a dichloromethane solution of phosphorus oxychloride (2 μl, 0.021 mmol) was dropwise added under cooling with ice. After stirring for 30 minutes, the suspension was diluted with ethyl acetate and poured into a saturated sodium hydrogen carbonate aqueous solution. Extraction with ethyl acetate was carried out twice, and the obtained organic layer was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=3:1) to give the desired compound 1,1′-[(1E,3E)-2,3-diisocyano-1,3-butadiene-1,4-diyl]bis[methoxybenzene] (2.2 mg, 72%) as liver brown solid.

Workup

  1. temperatureunder cooling with ice
  2. extractionExtraction with ethyl acetate
  3. concentrationthe obtained organic layer was concentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=3:1)

Sources & evidence

ORD record
ord-3f437cc3ca224a62929b5e9b5a7990f3
Source dataset
uspto-grants-2009_09
Patent number
US07595415B2

Reaction notes

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