Chloroacetyl chloride → 1,8-Bis(chloroacetamido)anthraquinone

HRID 556198

Reaction equation

HRID 556198 reaction equation
[NH2:1][C:2]1[C:15]2[C:14](=[O:16])[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][C:12]=3[NH2:17])[C:7](=[O:18])[C:6]=2[CH:5]=[CH:4][CH:3]=1.[Cl:19][CH2:20][C:21](Cl)=[O:22]>CN(C=O)C.N1C=CC=CC=1>[Cl:19][CH2:20][C:21]([NH:1][C:2]1[C:15]2[C:14](=[O:16])[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][C:12]=3[NH:17][C:21](=[O:22])[CH2:20][Cl:19])[C:7](=[O:18])[C:6]=2[CH:5]=[CH:4][CH:3]=1)=[O:22]

Participants

5

Reactant 2

HCID 6577Chloroacetyl chlorideHCID 85111,8-Diamino-9,10-anthracenedione

Product 1

HCID 469280411,8-Bis(chloroacetamido)anthraquinoneYield 80%

Reagents, catalysts & solvents 2

HCID 1049PyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

Dissolve 1,8-diaminoanthraquinone (0.476 g, 2.0 mmol) in 20 ml DMF. Add pyridine (0.5 ml) as catalyst in an ice bath. Then add chloroacetyl chloride (0.5 ml, 6 mmol) into the solution, remove the ice bath, introduce nitrogen, protect from light, and stir the solution at room temperature for 24 hours. The reacted solution is poured into ice water (50 ml), filtered to get precipitate. At last, the precipitate is recrystallized to get yellow compound 3.

Workup

  1. additionintroduce nitrogen
  2. filtrationfiltered
  3. customto get precipitate
  4. customAt last, the precipitate is recrystallized

Sources & evidence

ORD record
ord-9df7afb5faf0465792353d68acb00dbb
Source dataset
uspto-grants-2011_11
Patent number
US08053583B2

Linked notes

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