2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 178427047, compound

HRID 2054014Notes

Reaction equation

HRID 2054014 reaction equation
[Cl:1][C:2]1[CH:29]=[CH:28][C:5]2[NH:6][C:7]([CH:9]([NH:11][C:12](=[O:27])[C:13]3[CH:18]=[CH:17][C:16]([C:19]([N:21]4[CH2:25][CH:24]=[CH:23][CH2:22]4)=[O:20])=[C:15]([CH3:26])[CH:14]=3)[CH3:10])=[N:8][C:4]=2[CH:3]=1.ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl>O1CCOCC1>[Cl:1][C:2]1[CH:29]=[CH:28][C:5]2[NH:6][C:7]([CH:9]([NH:11][C:12](=[O:27])[C:13]3[CH:18]=[CH:17][C:16]([C:19]([N:21]4[CH:22]=[CH:23][CH:24]=[CH:25]4)=[O:20])=[C:15]([CH3:26])[CH:14]=3)[CH3:10])=[N:8][C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 178427048HCID 178427048, compound

Product 1

HCID 178427047HCID 178427047, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

200 mg (0.49 mmol) of rac.-N-[1-(5-chloro-1H-benzimidazol-2-yl)ethyl]-3-methyl-4-(2,5-dihydropyrrol-1-ylcarbonyl)benzamide and 167 mg (0.73 mmol) of 2,3-dichloro-5,6-dicyano-p-benzoquinone are stirred in 5 mL dioxane for 10 hours at 100° C. Then the solvent is distilled off and the residue is chromatographed on silica gel, eluting with dichloromethane/methanol (0%-6%). Yield: 30 mg (15%); Rf value: 0.62 (silica gel: dichloromethane/ethanol=9:1); C22H19ClN4O2 (406.875); mass spectrum: (M+H)+=407/409 (chlorine isotope).

Workup

  1. distillationThen the solvent is distilled off
  2. customthe residue is chromatographed on silica gel
  3. washeluting with dichloromethane/methanol (0%-6%)

Sources & evidence

ORD record
ord-cae510e836214589982cd2ace0ef27a2
Source dataset
uspto-grants-2008_02
Patent number
US07326791B2

Reaction notes

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