2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 136116400, compound

HRID 413972Notes

Reaction equation

HRID 413972 reaction equation
[CH2:1]([O:3][C:4]([CH:6]1[C:11](=[O:12])[NH:10][C:9]([S:13][CH3:14])=[N:8][CH:7]1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:5])[CH3:2].ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl>C(O)(C)C>[CH2:1]([O:3][C:4]([C:6]1[C:11](=[O:12])[NH:10][C:9]([S:13][CH3:14])=[N:8][C:7]=1[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 22597560HCID 22597560, compound

Product 1

HCID 136116400HCID 136116400, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of 5-ethyloxycarbonyl-2-methylthio-4-phenyl-4,5-dihydro-6-oxopyrimidine (273 mg) and 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (200 mg) in isopropanol (5 ml) was stirred for 16 h. The reaction mixture was evaporated to dryness, the residue was dissolved in dichloromethane and stirred with 5% sodium thiosulfate for 5 min. The organic layer was washed with 5% sodium bicarbonate and water (2×), dried over sodium sulfate and evaporated to dryness. The pure title compound was obtained after chromatography on silicagel in dichloromethane/methanol 98/2 (v/v) as eluent.

Workup

  1. customThe reaction mixture was evaporated to dryness
  2. dissolutionthe residue was dissolved in dichloromethane
  3. stirringstirred with 5% sodium thiosulfate for 5 min
  4. washThe organic layer was washed with 5% sodium bicarbonate and water (2×)
  5. dry with materialdried over sodium sulfate
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-d2c8042de90e488dbfa95d7253290bfb
Source dataset
uspto-grants-2003_05
Patent number
US06569863B1

Reaction notes

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