Hydrochloric Acid → HCID 178507708, compound

HRID 463562

Reaction equation

HRID 463562 reaction equation
ClCl.[CH:3]1[CH:8]=[C:7]2[C:9]([OH:20])=[C:10]3[C:15](=[C:16]([OH:17])[C:6]2=[CH:5][CH:4]=1)[C:14]([NH2:18])=[CH:13][CH:12]=[C:11]3[NH2:19].OS(O)(=O)=O.Cl.[NH2:27][C:28]1[C:41]2[C:40](=[O:42])[C:39]3[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=3)[C:33](=[O:43])[C:32]=2[CH:31]=[CH:30][CH:29]=1.[K]>O>[CH:3]1[CH:8]=[C:7]2[C:9]([C:10]3[C:15]([C:16](=[O:17])[C:6]2=[CH:5][CH:4]=1)=[C:14]([NH:18][C:31]1[CH:30]=[CH:29][C:28]([NH2:27])=[C:41]2[C:40]([C:39]4[C:34]([C:33](=[O:43])[C:32]=12)=[CH:35][CH:36]=[CH:37][CH:38]=4)=[O:42])[CH:13]=[CH:12][C:11]=3[NH2:19])=[O:20]

Participants

8

Reactant 6

HCID 313Hydrochloric AcidHCID 1118Sulfuric AcidHCID 67101-AminoanthraquinoneHCID 214029,10-Anthracenediol, 1,4-diamino-HCID 24526Chlorine2×HCID 5462222Potassium

Product 1

HCID 178507708HCID 178507708, compoundYield 103.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Chlorine is passed at 100° C. into a solution of 52.0 g of leuco-1,4-diaminoanthraquinone (94%) in 410 g of 96% strength H2SO4 until the leuco compound has just disappeared. Excess chlorine as well as hydrogen chloride is expelled by means of air. The batch is then allowed to cool down to room temperature, during which time 48.0 g of 1-aminoanthraquinone (98%) are added, and the mixture is then added dropwise to 410 g of water. 95.0 g of potassium peroxodisulphate are added in portions in the course of about 1 hour at 40°-50° C. to the paste. Stirring is allowed to continue for about 30 minutes at 30°-50° C., and the solids are filtered off with suction and washed with water until almost neutral. The press cake is washed with 300 ml of 10% strength NaHSO3 solution, and then with water, and dried at 100° C. 102.3 g of 4,4'-diamino-1,1'-dianthrimide (79% pure) are obtained; this result corresponds to 87% of theory.

Workup

  1. additionare added
  2. filtrationthe solids are filtered off with suction
  3. washwashed with water until almost neutral
  4. washThe press cake is washed with 300 ml of 10% strength NaHSO3 solution
  5. dry with materialwith water, and dried at 100° C

Sources & evidence

ORD record
ord-a4965a70162f4f74b2e6d5f87878b374
Source dataset
uspto-grants-1985_05
Patent number
US04520202

Linked notes

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