Hydrochloric Acid → HCID 178507708, compound

HRID 1262494Notes

Reaction equation

HRID 1262494 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 into a solution of 52.0 g of leuco-1,4-diaminoanthraquinone (94% pure ) in 410 g of 96% strength H2SO4 at 100° C. until the leuco compound has virtually completely disappeared. Excess chlorine and hydrogen chloride are blown out with air. The mixture is then allowed to cool down to room temperature while introducing 48.0 g of 1-aminoanthraquinone and the solution is then added dropwise to 410 g of water. 95.0 g of potassium peroxodisulphate are introduced in portions at 40°-50° C. within about 1 hour. The mixture is allowed to stir for approximately a further 30 minutes, the solid is filtered off with suction and washed with water until almost neutral. The filter 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), corresponding to 87% of theory, are obtained.

Workup

  1. filtrationthe solid is filtered off with suction
  2. washwashed with water until almost neutral
  3. washThe filter cake is washed with 300 ml of 10% strength NaHSO3 solution
  4. dry with materialwith water and dried at 100° C

Sources & evidence

ORD record
ord-4e7554c787d84b50a544ab83e5107ff3
Source dataset
uspto-grants-1984_06
Patent number
US04452742

Reaction notes

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