Potassium Hydroxide → HCID 58085460, compound

HRID 2232953Notes

Reaction equation

HRID 2232953 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([C:16]2[C:17]3[C:22]([CH:23]=[C:24]4[C:29]=2[CH:28]=[CH:27][CH:26]=[CH:25]4)=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:9]2[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][CH:10]=2)=[CH:4][CH:3]=1.[OH-].[K+].[Br:32]Br.S([O-])([O-])(=O)=S.[Na+].[Na+]>O1CCOCC1.O>[CH3:15][C:12]1[CH:13]=[CH:14][C:9]([N:8]([C:16]2[C:17]3[C:22]([C:23]([Br:32])=[C:24]4[C:29]=2[CH:28]=[CH:27][CH:26]=[CH:25]4)=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:5]2[CH:4]=[CH:3][C:2]([CH3:1])=[CH:7][CH:6]=2)=[CH:10][CH:11]=1

Participants

7

Reactant 4

HCID 14797Potassium HydroxideHCID 24408BromineHCID 24477Sodium ThiosulfateHCID 22976650N,N-Bis(4-methylphenyl)-9-anthracenamine

Product 1

HCID 58085460HCID 58085460, compoundYield 83.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

In a stream of nitrogen, 11.2 g (30 mmol) of 9-[N,N-bis(4-methylphenyl)amino]anthracene was dissolved in 100 ml of dioxane, and the whole was stirred at room temperature. Then, 1.68 g (30 mmol) of potassium hydroxide dissolved in 3 ml of water was added to the mixture dropwise. 5.75 g of bromine was added thereto, and the whole was stirred for 30 minutes. A 5% aqueous solution of sodium thiosulfate was added to the mixture, and the whole was stirred for 1 hour. The product was filtrated and washed with methanol. The product was recrystallized by using toluene, to thereby obtain 11.3 g of 9-[N,N-bis(4-methylphenyl)amino]-10-bromoanthracene.

Workup

  1. additionwas added to the mixture dropwise
  2. stirringthe whole was stirred for 30 minutes
  3. stirringthe whole was stirred for 1 hour
  4. filtrationThe product was filtrated
  5. washwashed with methanol
  6. customThe product was recrystallized

Sources & evidence

ORD record
ord-14be65013f1c4945b5f3e02495a2d4a0
Source dataset
uspto-grants-2010_05
Patent number
US07709104B2

Reaction notes

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