Pyridine → HCID 19901128, compound

HRID 1029796Notes

Reaction equation

HRID 1029796 reaction equation
[S:1]1[CH2:4][S:3][C:2]1=[C:5]([C:12]([OH:14])=O)[C:6]([O:8][CH:9]([CH3:11])[CH3:10])=[O:7].P(Cl)(Cl)(Cl)(Cl)Cl.N1C=CC=CC=1.[Cl:27][C:28]1[CH:34]=[CH:33][C:31]([NH2:32])=[CH:30][CH:29]=1>C(Cl)Cl>[S:3]1[CH2:4][S:1][C:2]1=[C:5]([C:12](=[O:14])[NH:32][C:31]1[CH:33]=[CH:34][C:28]([Cl:27])=[CH:29][CH:30]=1)[C:6]([O:8][CH:9]([CH3:10])[CH3:11])=[O:7]

Participants

6

Reactant 4

HCID 1049PyridineHCID 78124-ChloroanilineHCID 24819Phosphorus pentachlorideHCID 11776204130112-51-5

Product 1

HCID 19901128HCID 19901128, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of isopropyl 2-(1,3-dithietan-2-ylidene)-2-carboxyacetate (10 g) in methylene chloride (100 ml) was cooled to -10° C. and thereto phosphorous pentachloride (8.9 g) was added portionwise and then stirred for 1 hr. To the reaction mixture pyridine (13.8 ml) and 4-chloroaniline (5.45 g) were added and stirred for 2 hrs. The mixture was washed with dil-HCl, 10% aqueous sodium hydroxide solution and water and then evaporated. The residue was purified with ethyl acetate to afford the titled compound as a white solid. (8.9 g, 61%).

Workup

  1. stirringstirred for 2 hrs
  2. washThe mixture was washed with dil-HCl, 10% aqueous sodium hydroxide solution and water
  3. customevaporated
  4. customThe residue was purified with ethyl acetate

Sources & evidence

ORD record
ord-c0e4d7fb9b874b53b5b80be563296f43
Source dataset
uspto-grants-1992_04
Patent number
US05103013

Reaction notes

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