2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 13853742, compound

HRID 979311Notes

Reaction equation

HRID 979311 reaction equation
[Br:1][C:2]1[C:15]2[S:14](=[O:17])(=[O:16])[C:13]3[C:8](=[CH:9][CH:10]=[C:11]([O:18][CH3:19])[CH:12]=3)[NH:7][C:6]=2[CH:5]=[C:4]([O:20][CH3:21])[C:3]=1[OH:22].ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl>C1COCC1>[Br:1][C:2]1[C:3](=[O:22])[C:4]([O:20][CH3:21])=[CH:5][C:6]2[C:15]=1[S:14](=[O:16])(=[O:17])[C:13]1[C:8](=[CH:9][CH:10]=[C:11]([O:18][CH3:19])[CH:12]=1)[N:7]=2

Participants

4

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 13853740HCID 13853740, compound

Product 1

HCID 13853742HCID 13853742, compoundYield 30.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred suspension of 4-bromo-3-hydroxy-2,7-dimethoxy-10H-phenothiazin-5,5-dioxide (from Step 4) (1 g) in THF (10 ml) was added 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (1.17 g). After 15 minutes, the mixture was filtered, the solid washed with ether and air dried. The solid was filtered through a silica gel pad with CH2Cl2 :EtOAc, 1:1, to afford the title compound (300 mg), m.p. 228°-230° C. (dec), m/e 383.

Workup

  1. filtrationthe mixture was filtered
  2. washthe solid washed with ether and air
  3. customdried
  4. filtrationThe solid was filtered through a silica gel pad with CH2Cl2

Sources & evidence

ORD record
ord-6ccaf49162894e01bfb0e88821f50e3f
Source dataset
uspto-grants-1987_05
Patent number
US04667032

Reaction notes

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