2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 59822026, compound

HRID 1645322Notes

Reaction equation

HRID 1645322 reaction equation
[CH:1]1([CH:6]2[C:15]3[C:14](=[O:16])[CH2:13][C:12]([CH3:18])([CH3:17])[CH2:11][C:10]=3[NH:9][C:8]([CH:19]([CH3:21])[CH3:20])=[C:7]2[C:22](=[O:33])[C:23]2[CH:28]=[CH:27][C:26]([C:29]([F:32])([F:31])[F:30])=[CH:25][CH:24]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl>ClCCl>[CH:1]1([C:6]2[C:15]3[C:14](=[O:16])[CH2:13][C:12]([CH3:17])([CH3:18])[CH2:11][C:10]=3[N:9]=[C:8]([CH:19]([CH3:21])[CH3:20])[C:7]=2[C:22](=[O:33])[C:23]2[CH:28]=[CH:27][C:26]([C:29]([F:30])([F:31])[F:32])=[CH:25][CH:24]=2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

4

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 59822020HCID 59822020, compound

Product 1

HCID 59822026HCID 59822026, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4.0 g (8.7 mmol) of the compound from Example 1A are dissolved in 100 ml of dichloro-methane, and 2.17 g (9.6 mmol, 1.1 eq.) of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) are added a little at a time at 0° C. With stirring, the mixture is warmed to room temperature over a period of 3 h. The mixture is concentrated on a rotary evaporator and the residue is purified by chromatography (silica gel, mobile phase: isohexane/ethyl acetate 100:0→50:50).

Workup

  1. concentrationThe mixture is concentrated on a rotary evaporator
  2. customthe residue is purified by chromatography (silica gel, mobile phase: isohexane/ethyl acetate 100:0→50:50)

Sources & evidence

ORD record
ord-13d9f708df074d3c80534bb7bcf334a1
Source dataset
uspto-grants-2012_02
Patent number
US08124775B2

Reaction notes

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