2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 14652191, compound

HRID 1031419Notes

Reaction equation

HRID 1031419 reaction equation
[CH:1]([N:4]([CH:26]([CH3:28])[CH3:27])[C:5]([C@H:7]1[CH2:12][CH2:11][C@H:10]2[C@H:13]3[C@H:22]([CH2:23][CH2:24][C@:8]12[CH3:9])[C:21]1[CH:20]=[CH:19][C:18]([OH:25])=[CH:17][C:16]=1[CH2:15][CH2:14]3)=[O:6])([CH3:3])[CH3:2].ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl>O1CCOCC1.C(OCC)(=O)C>[CH:26]([N:4]([CH:1]([CH3:3])[CH3:2])[C:5]([C@H:7]1[CH2:12][CH2:11][C@H:10]2[C@H:13]3[C:22](=[CH:23][CH2:24][C@:8]12[CH3:9])[C:21]1[CH:20]=[CH:19][C:18]([OH:25])=[CH:17][C:16]=1[CH2:15][CH2:14]3)=[O:6])([CH3:27])[CH3:28]

Participants

5

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 18640900HCID 18640900, compound

Product 1

HCID 14652191HCID 14652191, compound

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of N,N-diisopropyl-estr-1,3,5(10)-triene-3-ol-17β-carboxamide (380 mg, 1 mmol) in 10 mL dioxane is treated with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (250 mg, 1.1 mmol) for two hours. The reaction mixture is diluted with ethyl acetate, washed with saturated aqueous NaHCO3, dried, and concentrated. Chromatography of the residue yields N,N-diisopropyl estr-1,3,5(10),9(11)-tetraene-3-ol-17β-carboxamide.

Workup

  1. washwashed with saturated aqueous NaHCO3
  2. customdried
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-37b5402eba7f4e7cbaf400f7678d4018
Source dataset
uspto-grants-1990_09
Patent number
US04954446

Reaction notes

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