Dimethylformamide → 1,5-Bis(p-hydroxyphenylthio)anthraquinone

HRID 1589879Notes

Reaction equation

Cl[C:2]1[C:15]2[C:14](=[O:16])[C:13]3[C:8](=[C:9](Cl)[CH:10]=[CH:11][CH:12]=3)[C:7](=[O:18])[C:6]=2[CH:5]=[CH:4][CH:3]=1.[OH:19][C:20]1[CH:25]=[CH:24][C:23]([SH:26])=[CH:22][CH:21]=1.[C:27](=[O:30])([O-])[O-].[K+].[K+].CN(C)C=O>O>[OH:19][C:20]1[CH:25]=[CH:24][C:23]([S:26][C:2]2[C:15]3[C:14](=[O:16])[C:13]4[C:8](=[C:9]([S:26][C:23]5[CH:24]=[CH:25][C:27]([OH:30])=[CH:21][CH:22]=5)[CH:10]=[CH:11][CH:12]=4)[C:7](=[O:18])[C:6]=3[CH:5]=[CH:4][CH:3]=2)=[CH:22][CH:21]=1

Participants

Conditions

Temperature: 145 °C

Procedure

A mixture of 27.7 grams (0.1 mole) of 1,5-dichloroanthraquinone, 28.5 grams (0.22 mole) of p-hydroxythiophenol, 30 grams (0.22 mole) of potassium carbonate, and 200 milliliters of dimethyl formamide was heated with stirring at 145° C. for 4 hours. The mixture was then cooled to room temperature, and poured into 1.5 liters of water. Thereafter, the above product was isolated by filtration, washed with 500 milliliters of water, and air dried. The product was then recrystallized from acetic acid to yield 30 grams of 1,5-bis(p-hydroxyphenylthio)anthraquinone as a yellow powder, m.p. (melting point) 298° to 300° C.; ms 456 (M+); vis (DMF), λmax 450 nm (nanometers) (ε 6300); Analysis Calculated for C26H16O4S2 : C, 68.4; H, 3.53; O, 14.02; S, 14.05. Found: C, 67.93; H, 3.60; O, 14.05; S, 14.26.

Workup

temperaturewas heated
temperatureThe mixture was then cooled to room temperature
customThereafter, the above product was isolated by filtration
washwashed with 500 milliliters of water, and air
customdried
customThe product was then recrystallized from acetic acid

Sources & evidence

ORD record: ord-0959019aae6149af855052f324b48f5a
Source dataset: uspto-grants-1993_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05200290

Reaction notes

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