2,6-Diaminopyridine → 2,6-Bis[2,2-bis(phenylsulphonyl)ethen-1-ylamino]pyridine

HRID 542892Notes

Reaction equation

HRID 542892 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([NH2:8])[N:3]=1.C(O[CH:12]=[C:13]([S:23]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)(=[O:25])=[O:24])[S:14]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)(=[O:16])=[O:15])C>C1(C)C=CC=CC=1>[C:17]1([S:14]([C:13]([S:23]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)(=[O:25])=[O:24])=[CH:12][NH:1][C:2]2[CH:7]=[CH:6][CH:5]=[C:4]([NH:8][CH:12]=[C:13]([S:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)(=[O:15])=[O:16])[S:23]([C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=3)(=[O:25])=[O:24])[N:3]=2)(=[O:15])=[O:16])[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

4

Reactant 2

HCID 88612,6-DiaminopyridineHCID 124009381,1-Bis(phenylsulphonyl)-2-ethoxyethene

Product 1

HCID 202074392,6-Bis[2,2-bis(phenylsulphonyl)ethen-1-ylamino]pyridineYield 22.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A stirred mixture of 2,6-diaminopyridine (0.3 g) and 2-ethoxy-1,1-bis(phenylsulphonyl)ethene (2.1 g) in toluene (50 ml) was heated at reflux for 2 hours. The mixture was cooled, and concentrated in vacuo, and the resulting solid was subjected to medium pressure chromatography on silica gel, eluting with acetone, to give 2,6-bis[2,2-bis(phenylsulphonyl)ethen-1-ylamino]pyridine (0.45 g), in the form of a white powder, m.p. 299°-300° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 2 hours
  3. temperatureThe mixture was cooled
  4. concentrationconcentrated in vacuo
  5. washeluting with acetone

Sources & evidence

ORD record
ord-18cc70f2b76b4e14855cab750cd09d2d
Source dataset
uspto-grants-1987_04
Patent number
US04659727

Reaction notes

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