Water → HCID 10347426, compound

HRID 257613Notes

Reaction equation

HRID 257613 reaction equation
Cl(O)(=O)(=O)=O.[NH2:6][CH2:7][C:8]1[CH:21]=[CH:20][C:19]2[C:10](=[C:11]3[C:16](=[CH:17][CH:18]=2)[CH:15]=[CH:14][C:13]([CH2:22][NH2:23])=[N:12]3)[N:9]=1.[C:24]1([CH3:34])[CH:29]=[CH:28][C:27]([S:30](Cl)(=[O:32])=[O:31])=[CH:26][CH:25]=1.[OH2:35]>N1C=CC=CC=1>[S:30]([NH:23][CH2:22][C:13]1[CH:14]=[CH:15][C:16]2[C:11](=[C:10]3[C:19](=[CH:18][CH:17]=2)[CH:20]=[CH:21][C:8]([CH2:7][NH:6][S:30]([C:27]2[CH:28]=[CH:29][C:24]([CH3:34])=[CH:25][CH:26]=2)(=[O:31])=[O:35])=[N:9]3)[N:12]=1)([C:27]1[CH:28]=[CH:29][C:24]([CH3:34])=[CH:25][CH:26]=1)(=[O:32])=[O:31]

Participants

5

Reactant 3

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 85665996144947-65-9

Product 1

HCID 10347426HCID 10347426, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

2,9-Bis(aminomethyl)-1,10-phenanthroline perchlorate (a) (1.76 g, 4 mmol) synthesized in Example 1(1) was dissolved in pyridine (20 ml). p-Toluenesulfonyl chloride (1.6 g, 8 mmol) was added to the solution with cooling using an ice bath, then the reaction mixture was stirred at room temperature for 3 hours. The resulting solution was poured into water (200 ml) and extracted with chloroform (200 ml). The chloroform layer was chromatographed on a silica gel column using chloroform/methanol as eluent to give the desired 2,9-bis(tosylaminomethyl)-1,10-phenanthroline (b) (yield=1.87 g).

Workup

  1. temperaturewith cooling
  2. extractionextracted with chloroform (200 ml)
  3. customThe chloroform layer was chromatographed on a silica gel column

Sources & evidence

ORD record
ord-03c36423822544a48ceb052f747a6594
Source dataset
uspto-grants-1993_11
Patent number
US05262526

Reaction notes

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