Water → HCID 58927072, compound

HRID 2400602Notes

Reaction equation

HRID 2400602 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([C:52]2[CH:57]=[CH:56][C:55]([CH3:58])=[CH:54][CH:53]=2)[C:9]2[CH:22]=[CH:21][C:20]3[C:19]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)(O)[C:18]4[C:13](=[CH:14][CH:15]=[C:16]([N:30]([C:38]5[CH:43]=[CH:42][C:41]([CH3:44])=[CH:40][CH:39]=5)[C:31]5[CH:36]=[CH:35][C:34]([CH3:37])=[CH:33][CH:32]=5)[CH:17]=4)[C:12]([C:46]4[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=4)(O)[C:11]=3[CH:10]=2)=[CH:4][CH:3]=1.[I-].[Na+].O.[PH2]([O-])=O.[Na+].O>C(O)(=O)C>[CH3:44][C:41]1[CH:40]=[CH:39][C:38]([N:30]([C:31]2[CH:36]=[CH:35][C:34]([CH3:37])=[CH:33][CH:32]=2)[C:16]2[CH:15]=[CH:14][C:13]3[C:18](=[C:19]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)[C:20]4[C:11]([C:12]=3[C:46]3[CH:47]=[CH:48][CH:49]=[CH:50][CH:51]=3)=[CH:10][C:9]([N:8]([C:5]3[CH:6]=[CH:7][C:2]([CH3:1])=[CH:3][CH:4]=3)[C:52]3[CH:57]=[CH:56][C:55]([CH3:58])=[CH:54][CH:53]=3)=[CH:22][CH:21]=4)[CH:17]=2)=[CH:43][CH:42]=1

Participants

6

Reactant 4

HCID 962WaterHCID 5238Sodium IodideHCID 67363459HCID 67363459, compoundHCID 178418950HCID 178418950, compound

Product 1

HCID 58927072HCID 58927072, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

The crude N,N,N′,N′-tetrakis(4-methylphenyl)-2,6-diamino-9,10-dihydro-9,10-diphenyl-9,10-anthracenediol was dissolved in 65 ml acetic acid. Sodium iodide (10 g), and sodium hypophosphite hydrate (10 g) were added with stirring. The mixture was heated to reflux for 60 minutes, cooled to room temperature and poured into water. The precipitated solid was collected by filtration, washed with water, washed with a small amount of methanol (˜5 ml) and then dried. Purification by column chromatography yielded 2.3 g (76% yield) of pure N,N,N′,N′-tetrakis(4-methylphenyl)-9,10-diphenyl-2,6-anthracenediamine (Inv-B73) as an orange solid. At a pressure of 600 mTorr, Inv-3 sublimed at 290° C. using train sublimation. FD-MS (m/z): 720.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 60 minutes
  3. filtrationThe precipitated solid was collected by filtration
  4. washwashed with water
  5. washwashed with a small amount of methanol (˜5 ml)
  6. customdried
  7. customPurification by column chromatography

Sources & evidence

ORD record
ord-17649b4c7be342f5952097eb26de6737
Source dataset
uspto-grants-2014_08
Patent number
US08795855B2

Reaction notes

Loading…