Hydrochloric Acid → HCID 70427322, compound

HRID 542887Notes

Reaction equation

HRID 542887 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.CO[CH:10]=[C:11]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[S:12]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)(=[O:14])=[O:13].CC(N(C)C)=O.Cl>C(OCC)C>[C:21]1([C:11]([S:12]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)(=[O:13])=[O:14])=[CH:10][NH:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=2)[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 104392-AminopyridineHCID 31374DimethylacetamideHCID 54191875HCID 54191875, compound

Product 1

HCID 70427322HCID 70427322, compoundYield 12.2%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of 2-aminopyridine (1.05 g) and 2-methoxy-1-phenyl-1-phenylsulphonylethene (2.0 g) in a mixture of anhydrous dimethylacetamide (50 ml) and a solution of hydrogen chloride in diethyl ether (6N; 0.5 ml) was heated at reflux for 25 hours, and then it was cooled and poured onto ice (150 g). The yellow precipitate was filtered off, subjected twice to medium pressure chromatography on silica gel, eluting with chloroform, triturated with light petroleum ether (b.p. 60°-80° C.) and recrystallised from a mixture of diethyl ether and light petroleum ether (b.p. 60°-80° C.), to give 1-phenyl-1-phenylsulphonyl-2-(pyrid-2-ylamino)ethene (0.3 g), m.p. 159°-160° C.

Workup

  1. temperatureat reflux for 25 hours
  2. temperatureit was cooled
  3. additionpoured onto ice (150 g)
  4. filtrationThe yellow precipitate was filtered off
  5. washeluting with chloroform
  6. customtriturated with light petroleum ether (b.p. 60°-80° C.)
  7. customrecrystallised from a mixture of diethyl ether and light petroleum ether (b.p. 60°-80° C.)

Sources & evidence

ORD record
ord-f4659a76b9b34f5694c0bd64b829ff8f
Source dataset
uspto-grants-1987_04
Patent number
US04659727

Reaction notes

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