2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 13240421, compound

HRID 979298Notes

Reaction equation

HRID 979298 reaction equation
[CH:1]1[C:14]2[C:5]([S:6][C:7]3[C:12]([N:13]=2)=[CH:11][CH:10]=[CH:9][CH:8]=3)=[CH:4][C:3](=[O:15])[CH:2]=1.C(N(CC)CC)C.[CH2:23]([SH:27])[CH2:24][CH2:25][CH3:26].ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl>CO>[CH2:23]([S:27][C:2]1[C:3](=[O:15])[CH:4]=[C:5]2[C:14](=[N:13][C:12]3[C:7]([S:6]2)=[CH:8][CH:9]=[CH:10][CH:11]=3)[CH:1]=1)[CH2:24][CH2:25][CH3:26]

Participants

6

Reactant 4

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 8012ButanethiolHCID 8471TriethylamineHCID 68485Phenothiazone

Product 1

HCID 13240421HCID 13240421, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 3H-phenothiazin-3-one (0.64 g) in 75 ml methanol was added triethylamine (1.0 ml) and n-butanethiol (0.58 ml). The mixture was stirred at room temperature for 48 hours. Then 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (0.67 g) was added. The mixture was stirred at room temperature for 2 hours. The solvent was removed in vacuo. The residue was chromatographed on neutral alumina (Act III) and eluted with 15% EtOAc/hexane to afford the title compound (0.4 g), m.p. 133° C.

Workup

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

Sources & evidence

ORD record
ord-edd57030c2714fa7a4270c077845220f
Source dataset
uspto-grants-1987_05
Patent number
US04667032

Reaction notes

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