2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 13853730, compound

HRID 979300Notes

Reaction equation

HRID 979300 reaction equation
[CH3:1][C:2]1[C:15](=[O:16])[CH:14]=[C:13]2[C:4](=[N:5][C:6]3[C:11]([S:12]2)=[CH:10][CH:9]=[CH:8][CH:7]=3)[CH:3]=1.C(N(CC)CC)C.[CH2:24]([SH:28])[CH2:25][CH2:26][CH3:27].ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl>ClC(Cl)C>[CH2:24]([S:28][C:14]1[C:15](=[O:16])[C:2]([CH3:1])=[CH:3][C:4]2[C:13]=1[S:12][C:11]1[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=1)[N:5]=2)[CH2:25][CH2:26][CH3:27]

Participants

6

Reactant 4

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 8012ButanethiolHCID 8471TriethylamineHCID 22311479HCID 22311479, compound

Product 1

HCID 13853730HCID 13853730, compound

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

To a solution of 2-methyl-phenothiazin-3-one (0.23 g) in 12 ml dichloroethane was added triethylamine (0.8 ml) and n-butanethiol (0.7 ml). The mixture was stirred at room temperature for 72 hours. 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone (0.22 g) was added. The mixture was stirred at room temperature for 2 hours. The mixture was stirred at room temperature for 2 hours. The solvent was removed in vacuo and the residue was chromatographed on neutral alumina (Act III) eluting with 15% EtOAc/hexane to give the title compound (120 mg), m.p. 97° C.

Workup

  1. stirringThe mixture was stirred at room temperature for 2 hours
  2. stirringThe mixture was stirred at room temperature for 2 hours
  3. customThe solvent was removed in vacuo
  4. customthe residue was chromatographed on neutral alumina (Act III)
  5. washeluting with 15% EtOAc/hexane

Sources & evidence

ORD record
ord-b3c0b1b1fad2498abebe0a489257f165
Source dataset
uspto-grants-1987_05
Patent number
US04667032

Reaction notes

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