Thionyl Chloride → 1,4-Diamino-2-chloroanthracene-9,10-dione

HRID 1731479Notes

Reaction equation

HRID 1731479 reaction equation
S(Cl)([Cl:3])=O.[NH2:5][C:6]1[C:19]2[C:18](=[O:20])[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11](=[O:21])[C:10]=2[C:9]([NH2:22])=[CH:8][CH:7]=1>>[Cl:3][C:8]1[CH:7]=[C:6]([NH2:5])[C:19]2[C:18](=[O:20])[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11](=[O:21])[C:10]=2[C:9]=1[NH2:22]

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 31420Disperse Violet 1

Product 1

HCID 183624121,4-Diamino-2-chloroanthracene-9,10-dioneYield 50%

Procedure

A mixture of thionyl chloride (320 g) and 1,4-diamino anthraquinone (20 g) is refluxed for 24 hours. The mixture is then cooled and poured onto crushed ice. The precipitate is filtered, dried and purified by recrystallization from carbon tetrachloride. The yield is 50 percent 2-chloro-1,4-diamino anthraquinone with a melting point of 207° C. to 210° C.

Workup

  1. temperatureis refluxed for 24 hours
  2. temperatureThe mixture is then cooled
  3. additionpoured
  4. customonto crushed ice
  5. filtrationThe precipitate is filtered
  6. customdried
  7. custompurified by recrystallization from carbon tetrachloride

Sources & evidence

ORD record
ord-8e52eff60e924f3faf3df838b33551cf
Source dataset
uspto-grants-1986_11
Patent number
US04622169

Reaction notes

Loading…