2,4,6-Trimethylaniline → HCID 21072034, compound

HRID 1372795Notes

Reaction equation

HRID 1372795 reaction equation
Br[C:2]1[C:15]2[C:14](=[O:16])[C:13]3[C:8](=[C:9](Br)[CH:10]=[C:11]([Br:17])[CH:12]=3)[C:7](=[O:19])[C:6]=2[CH:5]=[C:4]([Br:20])[CH:3]=1.[CH3:21][C:22]1[CH:27]=[C:26]([CH3:28])[C:25]([NH2:29])=[C:24]([CH3:30])[CH:23]=1.[C:31]([O-])(=O)[CH3:32].[Na+]>C([O-])(=O)C.[Cu+]>[C:24]1([CH3:30])[CH:23]=[C:22]([CH3:21])[CH:27]=[C:26]([CH3:28])[C:25]=1[NH:29][C:2]1[C:15]2[C:14](=[O:16])[C:13]3[C:8](=[C:9]([NH:29][C:25]4[C:24]([CH3:30])=[CH:23][C:22]([CH3:27])=[CH:21][C:31]=4[CH3:32])[CH:10]=[C:11]([Br:17])[CH:12]=3)[C:7](=[O:19])[C:6]=2[CH:5]=[C:4]([Br:20])[CH:3]=1

Participants

5

Reactant 3

HCID 69132,4,6-TrimethylanilineHCID 517045Sodium AcetateHCID 14150053HCID 14150053, compound

Product 1

HCID 21072034HCID 21072034, compound

Reagents, catalysts & solvents 1

HCID 69023Cuprous acetateCatalyst

Conditions

Temperature
170 °C

Procedure

37 g of 1,3,5,7-tetrabromoanthraquinone, 12.3 ml of mesidine, 17.3 g of sodium acetate and 0.5 g of copper(I) acetate are introduced into a laboratory reaction apparatus and stirred for 7 hours at 170° C. After cooling to RT, the crude product is precipitated by the addition of 1 liter of 2N HCl and recrystallised from ethanol. After filtration and drying 21 g (47%) of product are obtained.

Workup

  1. temperatureAfter cooling to RT
  2. customthe crude product is precipitated by the addition of 1 liter of 2N HCl
  3. customrecrystallised from ethanol
  4. filtrationAfter filtration
  5. dry with materialdrying 21 g (47%) of product
  6. customare obtained

Sources & evidence

ORD record
ord-b94493d987b541dfaa2ef7aedb8de1e2
Source dataset
uspto-grants-2007_01
Patent number
US07160335B2

Reaction notes

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