Dimethyl Sulfoxide → HCID 20227552, compound

HRID 1731480Notes

Reaction equation

CS(C)=O.Cl[C:6]1[CH:19]=[C:18]([NH2:20])[C:17]2[C:16](=[O:21])[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9](=[O:22])[C:8]=2[C:7]=1[NH2:23].[OH-:24].[Na+].[OH2:26]>>[OH:24][CH2:10][CH2:9][C:8]1[CH:17]=[CH:18][C:19]([O:26][C:6]2[CH:19]=[C:18]([NH2:20])[C:17]3[C:16](=[O:21])[C:15]4[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=4)[C:9](=[O:22])[C:8]=3[C:7]=2[NH2:23])=[CH:6][CH:7]=1

Participants

Reactant 4

HCID 679Dimethyl Sulfoxide

HCID 962Water2×

HCID 14798Sodium Hydroxide

HCID 183624121,4-Diamino-2-chloroanthracene-9,10-dione

Product 1

HCID 20227552HCID 20227552, compoundYield 24%

Procedure

A solution of dimethylsulfoxide (50 ml), water (5.0 ml), 2-chloro-1,4-diamino anthraquinone (5.0 g) and sodium hydroxide (1.0 g) is heated to 100° C. for 4 hours. The mixture is cooled and diluted with water until a precipitate forms. The precipitate is collected, washed, dried and recrystallized from carbon tetrachloride. The yield is 24 percent 2-(p-hydroxy ethyl phenoxy)-1,4-diamino anthraquinone with a melting point of 224° C. to 227° C.

Workup

temperatureThe mixture is cooled
customThe precipitate is collected
washwashed
customdried
customrecrystallized from carbon tetrachloride

Sources & evidence

ORD record: ord-0a2644fce8bf4010a21ebf66bc02d66a
Source dataset: uspto-grants-1986_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04622169

Reaction notes

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