Dichloromethane → HCID 19770956, compound

HRID 1589844Notes

Reaction equation

HRID 1589844 reaction equation
C([O-])([O-])=O.[Na+].[Na+].[I-].[NH2:8][N+:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH2:15][CH2:16][CH3:17].[C:18]([O:22][CH2:23][CH3:24])(=[O:21])[C:19]#[CH:20].C(Cl)Cl>CN(C=O)C>[CH2:15]([C:10]1[N:9]2[N:8]=[CH:20][C:19]([C:18]([O:22][CH2:23][CH3:24])=[O:21])=[C:14]2[CH:13]=[CH:12][CH:11]=1)[CH2:16][CH3:17]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 10340Sodium CarbonateHCID 12182Ethyl propiolateHCID 19770970HCID 19770970, compound

Product 1

HCID 19770956HCID 19770956, compoundYield 33.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Next, 2.41 g (22.7 mmol) of Na2CO3 were added to a solution of 5.0 g (18.9 mmol) of 1-amino-2-propylpyridinium iodide in 20 ml of DMF, followed by stirring at room temperature for 1 hour. Ethyl propiolate (3.71 g; 37.9 mmol) was added further, followed by stirring at room temperature for 20 hours. After the reaction, the reaction mixture was treated in a similar manner to the preparation of the 7-ethyl derivative, whereby 1.45 g (6.25 mmol) of the title compound were obtained as crystals from CH2Cl2 :hexane=1:1 eluate fractions (yield: 33% - 9% in two steps).

Workup

  1. stirringby stirring at room temperature for 20 hours
  2. customAfter the reaction

Sources & evidence

ORD record
ord-58575ed3541f4eab9874d4edca8b8203
Source dataset
uspto-grants-1993_04
Patent number
US05200415

Reaction notes

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