2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 58158151, compound

HRID 1916268Notes

Reaction equation

HRID 1916268 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:9][CH:10]=[C:11]([CH2:13][S:14][C:15]3[NH:16][C:17]4[CH2:18][CH2:19][CH2:20][C:21](=[O:39])[C:22]=4[CH:23]([C:27]4[CH:32]=[CH:31][C:30]([O:33][CH2:34][C@@H:35]([OH:38])[CH2:36][OH:37])=[CH:29][CH:28]=4)[C:24]=3[C:25]#[N:26])[N:12]=2)=[CH:4][CH:3]=1.ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl>ClCCl.O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:9][CH:10]=[C:11]([CH2:13][S:14][C:15]3[C:24]([C:25]#[N:26])=[C:23]([C:27]4[CH:28]=[CH:29][C:30]([O:33][CH2:34][C@@H:35]([OH:38])[CH2:36][OH:37])=[CH:31][CH:32]=4)[C:22]4[C:21](=[O:39])[CH2:20][CH2:19][CH2:18][C:17]=4[N:16]=3)[N:12]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 58158136HCID 58158136, compound

Product 1

HCID 58158151HCID 58158151, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

At RT, 100 mg (0.172 mmol) of the compound from Example 5A and 40 mg (0.174 mmol) of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone were stirred overnight in 6 ml of dichloromethane. The reaction solution was diluted with dichloromethane and water, and the two phases were separated. The aqueous phase was extracted twice with dichloromethane. The combined organic phases were concentrated and purified by preparative HPLC (Chromasil, water/acetonitrile+0.1% TFA).

Workup

  1. customthe two phases were separated
  2. extractionThe aqueous phase was extracted twice with dichloromethane
  3. concentrationThe combined organic phases were concentrated
  4. custompurified by preparative HPLC (Chromasil, water/acetonitrile+0.1% TFA)

Sources & evidence

ORD record
ord-6026597a06ea4698b7df8b004cd7eba4
Source dataset
uspto-grants-2013_12
Patent number
US08618119B2

Reaction notes

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