2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 86675237, compound

HRID 2370061Notes

Reaction equation

HRID 2370061 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([CH3:8])[N:5]=[C:4]([NH:9][CH2:10][CH2:11][S:12][CH3:13])[C:3]=1[NH2:14].[Cl:15][C:16]1[CH:23]=[CH:22][CH:21]=[CH:20][C:17]=1[CH:18]=O.ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl>O1CCOCC1.ClCCl>[Cl:1][C:2]1[N:7]=[C:6]([CH3:8])[N:5]=[C:4]2[C:3]=1[N:14]=[C:18]([C:17]1[CH:20]=[CH:21][CH:22]=[CH:23][C:16]=1[Cl:15])[N:9]2[CH2:10][CH2:11][S:12][CH3:13]

Participants

6

Reactant 3

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 69962-ChlorobenzaldehydeHCID 86675236HCID 86675236, compound

Product 1

HCID 86675237HCID 86675237, compoundYield 76.8%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

Heat a mixture of 6-chloro-2-methyl-N4-(2-methylsulfanylethyl)pyrimidine-4,5-diamine (1.63 g, 0.007 mol), 2-chlorobenzaldehyde (1.96 g, 0.014 mol), and 15% FeCl3 on SiO2 (4.89 g) in 1,4-dioxane (15 mL) to 100° C. for 16 h. Cool the reaction and remove the silica by filtration through diatomaceous earth. Concentrate the filtrate under reduced pressure to give a residue. Dissolve the residue in dry dichloromethane (10 mL) and add 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (1.58 g, 0.007 mol) at 0° C. Stir the reaction mixture at room temperature for 2 h. Dilute the reaction mixture with dichloromethane, and wash with 1 N aqueous sodium hydroxide solution, water and brine. Dry the organic layer over anhydrous sodium sulfate, filter, and concentrate to give a residue. Purify the residue on a silica gel column eluting with ethyl acetate:hexane (15:85) to give the title compound (1.9 g). ES/MS m/z 353 (M+1).

Workup

  1. temperatureHeat
  2. temperatureCool
  3. customthe reaction
  4. customremove the silica
  5. filtrationby filtration through diatomaceous earth
  6. concentrationConcentrate the filtrate under reduced pressure
  7. customto give a residue
  8. washwash with 1 N aqueous sodium hydroxide solution, water and brine
  9. dry with materialDry the organic layer over anhydrous sodium sulfate
  10. filtrationfilter
  11. concentrationconcentrate
  12. customto give a residue
  13. customPurify the residue on a silica gel column
  14. washeluting with ethyl acetate:hexane (15:85)

Sources & evidence

ORD record
ord-c8485b98c9b941059d4a60c81b8f9bf2
Source dataset
uspto-grants-2014_04
Patent number
US08710063B2

Reaction notes

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