2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 21109091, compound

HRID 1766079Notes

Reaction equation

HRID 1766079 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:7]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([O:21][CH3:22])[CH:16]=2)[N:8]=[C:9]([S:13][CH3:14])[NH:10][C:11]=1[CH3:12])=[O:5])[CH3:2].ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl.[OH-].[Na+]>C1(C)C=CC=CC=1.C(Cl)Cl>[CH3:14][S:13][C:9]1[N:8]=[C:7]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([O:21][CH3:22])[CH:16]=2)[C:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])=[C:11]([CH3:12])[N:10]=1

Participants

6

Reactant 3

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 14798Sodium HydroxideHCID 21109090HCID 21109090, compound

Product 1

HCID 21109091HCID 21109091, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

Ethyl-2-methylthio-4-(3-methoxyphenyl)-6-methyl-1,4-dihydro-pyrimidine-5-carboxylate (example 24a, 7.65 g) was dissolved in a mixture of toluene (200 ml) and CH2Cl2 (100 ml). 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone (5.45 g) was added and the reaction mixture was stirred at room temperature for 15 min. 0.2M aq. NaOH (250 ml) was added. The organic layer was separated, washed with H2O (2*250 ml) and sat. aq. NaCl (2*250 ml), dried (MgSO4) and concentrated under reduced pressure. The title compound was purified by chromatography on silica gel with hept/EtOAc=4/1 (v/v) as eluent.

Workup

  1. customThe organic layer was separated
  2. washwashed with H2O (2*250 ml) and sat. aq. NaCl (2*250 ml)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated under reduced pressure
  5. customThe title compound was purified by chromatography on silica gel with hept/EtOAc=4/1 (v/v) as eluent

Sources & evidence

ORD record
ord-88dded3ba2414d7d94c4357f9e791384
Source dataset
uspto-grants-2007_06
Patent number
US07229990B2

Reaction notes

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