Dimethylamine → 1,8-Bis[2-(Dimethylamino)Acetamido]Anthraquinone

HRID 556201Notes

Reaction equation

HRID 556201 reaction equation
Cl[CH2:2][C:3]([NH:5][C:6]1[C:19]2[C:18](=[O:20])[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][C:16]=3[NH:21][C:22](=[O:25])[CH2:23]Cl)[C:11](=[O:26])[C:10]=2[CH:9]=[CH:8][CH:7]=1)=[O:4].[CH3:27][NH:28][CH3:29].[CH3:30][N:31](C)[CH:32]=O>>[CH3:27][N:28]([CH3:29])[CH2:2][C:3]([NH:5][C:6]1[C:19]2[C:18](=[O:20])[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][C:16]=3[NH:21][C:22](=[O:25])[CH2:23][N:31]([CH3:32])[CH3:30])[C:11](=[O:26])[C:10]=2[CH:9]=[CH:8][CH:7]=1)=[O:4]

Participants

4

Reactant 3

HCID 674DimethylamineHCID 6228DimethylformamideHCID 469280411,8-Bis(chloroacetamido)anthraquinone2×

Product 1

HCID 462447761,8-Bis[2-(Dimethylamino)Acetamido]AnthraquinoneYield 64%

Procedure

Add 0.4 g, 1.0 mmol 1,8-bis(chloroacetamido)anthraquinone (compound 3) with 0.5 ml TEA, and 0.4 ml, 6 mmole Dimethylamine, dissolved in 20 ml dehydrated dimethylformamide (DMF). The mixture is reacted in a mini-reactor. The reaction temperature is 120° C. in the oil bath and the reaction time is 30 minutes. The reacted mixture is poured into 50 ml ice water and is filtered to collect precipitate. The precipitate is recrystallized from ethanol to get yellow compound 3m.

Workup

  1. customThe mixture is reacted in a mini-reactor
  2. customis 120° C. in the oil bath
  3. filtrationis filtered
  4. customto collect precipitate
  5. customThe precipitate is recrystallized from ethanol

Sources & evidence

ORD record
ord-b631d1cb907d4cb29dd2b848df957315
Source dataset
uspto-grants-2011_11
Patent number
US08053583B2

Reaction notes

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