Hydrochloric Acid → HCID 19090664, compound

HRID 1463544Notes

Reaction equation

HRID 1463544 reaction equation
Cl[C:2]1[C:19](Cl)=[CH:18][C:17]2[C:16](=[O:21])[C:15]3[C:6](=[C:7]([OH:25])[C:8]4[C:13]([C:14]=3[OH:22])=[CH:12][C:11](Cl)=[C:10](Cl)[CH:9]=4)[C:5](=[O:26])[C:4]=2[CH:3]=1.[C:27]1([SH:33])[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.C(=O)([O-])[O-].[K+].[K+].Cl>CS(C)=O>[C:27]1([S:33][C:2]2[C:19]([S:33][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[CH:18][C:17]3[C:16](=[O:21])[C:15]4[C:6](=[C:7]([OH:25])[C:8]5[C:13]([C:14]=4[OH:22])=[CH:12][C:11]([S:33][C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)=[C:10]([S:33][C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)[CH:9]=5)[C:5](=[O:26])[C:4]=3[CH:3]=2)[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7969ThiophenolHCID 11430Potassium CarbonateHCID 3091929HCID 3091929, compound

Product 1

HCID 19090664HCID 19090664, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

50 g (116.8 mmol) of 2,3,8,9-tetrachloro-6,11-dihydroxynaphthacene-5,12-dione, 77.22 g (700.8 mmol) of thiophenol, 129.15 g (934 mmol) of potassium carbonate and 400 ml of dimethyl sulfoxide (DMSO) are stirred for 1 day at 100° C. The mixture is poured into a dilute aqueous solution of HCl and stirred. The red crude product is isolated by filtration, washed with water, dried at 140° C. under vacuum, then extracted three times by boiling with cyclohexanone and dried once more. Yield: 80.11 g (95%); melting point >260° C. MS: 722 (M+ ; base peak).

Sources & evidence

ORD record
ord-01b4f50a0f6b4e66b18fc00cefbee281
Source dataset
uspto-grants-1994_04
Patent number
US05300663

Reaction notes

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