Water → HCID 19045304, compound

HRID 1591172Notes

Reaction equation

HRID 1591172 reaction equation
[ClH:1].[NH:2]1[CH2:7][CH2:6][C:5]2([CH2:12][C:11](=[O:13])[C:10]3[CH:14]=[CH:15][CH:16]=[CH:17][C:9]=3[S:8]2)[CH2:4][CH2:3]1.[CH:18]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=1)=[CH2:19].C([O-])(O)=O.[Na+].O>C(O)C.C(O)(=O)C>[ClH:1].[N:21]1[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=1[CH2:18][CH2:19][N:2]1[CH2:7][CH2:6][C:5]2([CH2:12][C:11](=[O:13])[C:10]3[CH:14]=[CH:15][CH:16]=[CH:17][C:9]=3[S:8]2)[CH2:4][CH2:3]1

Participants

7

Reactant 4

HCID 962WaterHCID 75212-Vinylpyridine2×HCID 516892Sodium BicarbonateHCID 19766242HCID 19766242, compound

Product 1

HCID 19045304HCID 19045304, compoundYield 82.7%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 702EthanolSolvent

Procedure

Under N2, a mixture of product from Step D (0.54 g, 0.002 mol), 2-vinylpyridine (0.62 g, 0.0059 mol), NaHCO3 (0.6 g, 0.0071 mol) in absolute ethanol (20 ml) was heated at reflux. After 24 hours, acetic acid (4 drops) was added and refluxing was continued. After 24 hours, H2O (20 ml), and 2-vinylpyridine (2 ml) were added. After another 72 hours at reflux, the reaction was concentrated to dryness. The residue was chromatographed on silica gel (Still column, 50 mm) and the product eluted with 5% CH3OH--CHCl3. The compound was crystallized as the hydrochloride salt from ethanol to yield 0.62 g (80%) of product.

Workup

  1. temperaturewas heated
  2. temperatureat reflux
  3. temperaturerefluxing
  4. waitAfter 24 hours
  5. temperatureAfter another 72 hours at reflux
  6. concentrationthe reaction was concentrated to dryness
  7. customThe residue was chromatographed on silica gel (Still column, 50 mm) and the product
  8. washeluted with 5% CH3OH
  9. customThe compound was crystallized as the hydrochloride salt from ethanol

Sources & evidence

ORD record
ord-557593d11ac94b60b459a5c10def3cc0
Source dataset
uspto-grants-1993_04
Patent number
US05206240

Reaction notes

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