2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 58459057, compound

HRID 408809Notes

Reaction equation

HRID 408809 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([CH3:8])[N:5]=[C:4]([NH:9][CH2:10][CH2:11][O: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.C(C1C(=O)C(Cl)=C(Cl)C(=O)C=1C#N)#N>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][O:12][CH3:13]

Participants

6

Reactant 3

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 69962-ChlorobenzaldehydeHCID 584590916-Chloro-N4-(2-methoxyethyl)-2-methylpyrimidine-4,5-diamine

Product 1

HCID 58459057HCID 58459057, compoundYield 37.4%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

Heat a solution of 6-chloro-N4-(2-methoxyethyl)-2-methylpyrimidine-4,5-diamine (5.0 g, 0.023 mol), 2-chlorobenzaldehyde (4.8 g, 0.03 mol), 15% FeCl3 on SiO2 (20 g) in 1,4-dioxane (150 mL) to 100° C. for 16 h. Remove the silica by filtration through diatomaceous earth, and concentrate the filtrate under reduced pressure to give a residue. Dissolve the residue in dry dichloromethane (150 mL) and add DDQ (5.2 g, 0.022 mol) at 0° C., and stir the reaction mixture at room temperature for 2 h. Dilute the reaction mixture with dichloromethane, wash with 1 N 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:n-hexane (40:60) to give the title compound (2.9 g). ES/MS m/z 337 (M+1).

Workup

  1. customRemove the silica
  2. filtrationby filtration through diatomaceous earth
  3. concentrationconcentrate the filtrate under reduced pressure
  4. customto give a residue
  5. washwash with 1 N sodium hydroxide solution, water, and brine
  6. dry with materialDry the organic layer over anhydrous sodium sulfate
  7. filtrationfilter
  8. concentrationconcentrate
  9. customto give a residue
  10. customPurify the residue on a silica gel column
  11. washeluting with ethyl acetate:n-hexane (40:60)

Sources & evidence

ORD record
ord-49fb5343fcf14ed7a0a9b07d24a6971e
Source dataset
uspto-grants-2014_06
Patent number
US08759360B2

Reaction notes

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