2,3-Epoxy-2,3-dihydro-1,4-naphthoquinone → HCID 178516903, compound

HRID 622398Notes

Reaction equation

HRID 622398 reaction equation
[O:1]1[CH:11]2[CH:2]1[C:3](=[O:13])[C:4]1[C:9]([C:10]2=[O:12])=[CH:8][CH:7]=[CH:6][CH:5]=1.[N:14]1([C:20]2[O:21][C:22]3[CH:28]=[CH:27][CH:26]=[CH:25][C:23]=3[N:24]=2)[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1>C(O)C>[O:21]1[C:22]2[CH:28]=[CH:27][CH:26]=[CH:25][C:23]=2[N:24]=[C:20]1[N:14]1[CH2:15][CH2:16][N:17]([C:2]2[C:3](=[O:13])[C:4]3[C:9]([C:10](=[O:12])[C:11]=2[OH:1])=[CH:8][CH:7]=[CH:6][CH:5]=3)[CH2:18][CH2:19]1

Participants

4

Reactant 2

HCID 858442,3-Epoxy-2,3-dihydro-1,4-naphthoquinoneHCID 6478182-(Piperazin-1-yl)-1,3-benzoxazole

Product 1

HCID 178516903HCID 178516903, compoundYield 14.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 3.48 g of 2,3-epoxy-2,3-dihydro-1,4-naphthoquinone, 2.03 g of 2-(1-piperazinyl)benzoxazole and 200 ml of absolute ethanol was stirred 18 hours and then filtered. The filtrate was concentrated to dryness and the residue flash chromatographed, eluting with dichloromethane, then 1% methanol in dichloromethane. The desired fraction was evaporated, then recrystallized twice from dichloromethane/ethanol, giving 533 mg of the desired product, mp 190°C. (dec.).

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated to dryness
  3. customthe residue flash chromatographed
  4. washeluting with dichloromethane
  5. customThe desired fraction was evaporated
  6. customrecrystallized twice from dichloromethane/ethanol

Sources & evidence

ORD record
ord-c9c275ee3d4048caafed3b4a8ac326c2
Source dataset
uspto-grants-1988_09
Patent number
US04771061

Reaction notes

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