Dichloromethane → HCID 86626447, compound

HRID 736857Notes

Reaction equation

HRID 736857 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 86626448HCID 86626448, compound

Product 1

HCID 86626447HCID 86626447, compoundYield 59.1%

Reagents, catalysts & solvents 3

HCID 1049PyridineSolventHCID 6212ChloroformSolventHCID 8857Ethyl AcetateSolvent

Procedure

1,1′-[(1Z,3Z)-2,3-diformylamino-1,3-butadiene-1,4-diyl]bis[methoxybenzene] (11.0 mg, 0.031 mmol) prepared in Reference Synthetic Example 4 was suspended in chloroform (200 μl) and pyridine (200 μl), and a dichloromethane solution of phosphorus oxychloride (6.4 μl, 0.069 mmol) was dropwise added under cooling with ice. After stirring for 45 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=5:1) to give the desired compound 1,1′-[(1Z,3Z)-2,3-diisocyano-1,3-butadiene-1,4-diyl]bis[methoxybenzene] (xanthocillin X dimethyl ether) (5.8 mg, 59%) as pale green crystals.

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=5:1)

Sources & evidence

ORD record
ord-da68ede1a2a24c3a83236cd619777e09
Source dataset
uspto-grants-2009_09
Patent number
US07595415B2

Reaction notes

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