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

HRID 868199Notes

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-1b4fd5fc5da346a18a2d95eba0c94813
Source dataset: uspto-grants-1988_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04778742

Reaction notes

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