2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 16064939, compound

HRID 1991127Notes

Reaction equation

HRID 1991127 reaction equation
ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl.[N:15]1([CH2:24][C:25]2[CH:26]=[C:27]3[C:33]([C:34]4[CH:35]=[N:36][N:37]([CH3:39])[CH:38]=4)=[CH:32][NH:31][C:28]3=[N:29][CH:30]=2)[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH2:17][CH2:16]1.C([O-])(O)=O.[Na+]>C(Cl)Cl>[N:15]1([CH2:24][C:25]2[CH:26]=[C:27]3[C:33]([C:34]4[CH:35]=[N:36][N:37]([CH3:39])[CH:38]=4)=[CH:32][NH:31][C:28]3=[N:29][CH:30]=2)[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:17]=[CH:16]1

Participants

5

Reactant 3

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 516892Sodium BicarbonateHCID 16064801HCID 16064801, compound

Product 1

HCID 16064939HCID 16064939, compoundYield 26.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2,3-Dichloro-5,6-dicyano-1,4-benzoquinone (25 mg, 0.11 mmol) was added in small portions over a period of 0.5 h to a stirred solution of 59 (11.0 mg, 33.4 μmol) in CH2Cl2 (1.8 mL)-0.2 M aqueous phosphate buffer (pH 7.0) solution (0.05 mL). When the addition was completed, the mixture was stirred for additional 0.5 h and then treated with saturated aqueous NaHCO3 (2 mL). Stirring continued for 1 h. The organic layer was separated and the aqueous phase extracted with CH2Cl2 (5×2 mL). Combined organic solutions were washed with brine, dried (MgSO4), concentrated and the residue was purified by means of PTLC using AcOEt as eluent to afford 60 (2.9 mg, 26%) as grey solid; 1H NMR (400 MHz, CDCl3) δ 3.95 (s, 3H), 5.46 (s, 2H), 6.56 (dd, J=3.2, 0.7 Hz, 1H), 7.12 (td, J=7.5, 1.0 Hz, 1H), 7.16 (d, J=3.2, 1H), 7.20 (td, J=7.5, 1.2 Hz, 1H), 7.37 (d, J=2.4 Hz, 1H), 7.39 (dd, J=8.2, 0.7 Hz, 1H), 7.47 (s, 1H), 7.66 (s, 1H), 7.66 (dd, J=7.8, 0.7 Hz, 1H), 7.82 (d, J=1.9 Hz, 1H), 8.28 (d, J=1.9 Hz, 1H), 8.86 (bs, 1H).

Workup

  1. additionWhen the addition
  2. stirringStirring
  3. waitcontinued for 1 h
  4. customThe organic layer was separated
  5. extractionthe aqueous phase extracted with CH2Cl2 (5×2 mL)
  6. washCombined organic solutions were washed with brine
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated
  9. customthe residue was purified by means of PTLC

Sources & evidence

ORD record
ord-cfcee39001404135a55e11370360bd95
Source dataset
uspto-grants-2010_01
Patent number
US07645769B2

Reaction notes

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