2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 13853729, compound

HRID 979299Notes

Reaction equation

HRID 979299 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>C1COCC1>[CH2:23]([S:27][C:4]1[C:3](=[O:15])[CH:2]=[CH:1][C:14]2[C:5]=1[S:6][C:7]1[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=1)[N:13]=2)[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 13853729HCID 13853729, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of phenothiazin-3-one (0.21 g) in 20 ml THF was added triethylamine (0.28 ml) and n-butanethiol (0.2 ml). The mixture was refluxed for 15 hours and then cooled to room temperature. 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) (0.22 g) was added and the reaction was stirred for 2 hours at 25°. 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, m.p. 72° C.

Workup

  1. temperatureThe mixture was refluxed for 15 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-e1f146fcde7c4a53a3a11ce46337a7d6
Source dataset
uspto-grants-1987_05
Patent number
US04667032

Reaction notes

Loading…