Dichloromethane → 1,4-Naphthoquinone

HRID 1284885Notes

Reaction equation

HRID 1284885 reaction equation
[N+](C1C=CC(N(C[C:15]2[C:16](=[O:42])[C:17]3[C:22]([C:23](=[O:41])[C:24]=2CCCCCCCCCCCCCCCC)=[CH:21][CH:20]=[CH:19][CH:18]=3)C(Cl)=O)=CC=1)([O-])=O.ClCCl>N1C=CC=CC=1.C(OCC)(=O)C>[CH:19]1[CH:20]=[CH:21][C:22]2[C:23](=[O:41])[CH:24]=[CH:15][C:16](=[O:42])[C:17]=2[CH:18]=1

Participants

5

Reactant 2

HCID 6344DichloromethaneHCID 20250611HCID 20250611, compound

Product 1

HCID 85301,4-NaphthoquinoneYield 60%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Procedure

N-4-Nitrophenyl-N-(3-hexadecyl-1,4-naphthoquinonylmethyl)carbamoyl chloride (6.72 g, 11.3 mmol) was dissolved in 10 ml dry pyridine, using a minimum quantity of dichloromethane to aid in dissolution. The dye (as the methylsulfamoyl form) ##STR8## (4.2 g, 4.72 mmol) was then added and the resulting solution was stirred at room temperature overnight. The mixture was then diluted with ethyl acetate, extracted with 2N hydrochloric acid, dried with anhydrous magnesium sulfate, and filtered. The ethyl acetate was removed in vacuo and the residue was dissolved in 20 percent ethyl acetate in toluene. This solution was passed through a short column of silica gel, eluting first with 20 percent ethyl acetate in toluene to remove some impurities, then with 30 percent ethyl acetate in toluene. This second elutant was concentrated under reduced pressure to yield the crude product (60 percent).

Workup

  1. dissolutionto aid in dissolution
  2. extractionextracted with 2N hydrochloric acid
  3. dry with materialdried with anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customThe ethyl acetate was removed in vacuo
  6. dissolutionthe residue was dissolved in 20 percent ethyl acetate in toluene
  7. washeluting first with 20 percent ethyl acetate in toluene
  8. customto remove some impurities
  9. concentrationThis second elutant was concentrated under reduced pressure

Sources & evidence

ORD record
ord-c87c45a91f2142a49aab2f136f45a7ab
Source dataset
uspto-grants-1986_01
Patent number
US04564577

Reaction notes

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