Hydrochloric Acid → HCID 67336959, compound

HRID 1678326Notes

Reaction equation

HRID 1678326 reaction equation
[Cl-:1].[NH3+:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]([C:9]1[CH:10]=[NH+:11][CH:12]=[CH:13][CH:14]=1)=O.[Cl-].[CH:16]([C:18]1[O:22][C:21]([C:23]2[CH:27]=[CH:26][S:25][C:24]=2[C:28]([O:30][CH3:31])=[O:29])=[CH:20][CH:19]=1)=O.Cl>C(O)(C)C>[ClH:1].[ClH:1].[N:11]1[CH:12]=[CH:13][CH:14]=[C:9]([C:7]2[C:6](=[CH:16][C:18]3[O:22][C:21]([C:23]4[CH:27]=[CH:26][S:25][C:24]=4[C:28]([O:30][CH3:31])=[O:29])=[CH:20][CH:19]=3)[CH2:5][CH2:4][CH2:3][N:2]=2)[CH:10]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 2797068Methyl 3-(5-formylfuran-2-yl)thiophene-2-carboxylateHCID 673376573-(5-Ammoniopentanoyl)pyridinium chloride

Product 1

HCID 67336959HCID 67336959, compoundYield 97.7%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
80 °C

Procedure

3-(5-Ammoniopentanoyl)pyridinium chloride (99 mg, 0.39 mmol) and methyl 3-(5-formyl-2-furyl)thiophene-2-carboxylate (102 mg, 0.43 mmol) were combined in a reaction vessel and treated with isopropanol (6 mL). The reaction vessel was sealed and the reaction was heated to 80° C. with stirring overnight. The reaction was cooled to room temperature. The precipitate was recovered by vacuum filtration, then treated with saturated NaHCO3(aq) and extracted three times with EtOAc. The EtOAc extracts were washed with brine, combined, dried over Na2SO4, filtered, concentrated under reduced pressure, and eluted through a 20 gram column of silica gel with 99:1:0.1 CH2Cl2:MeOH:NH4OH (1 liter). The recovered material was dissolved into MeOH and treated with 2 eq. of 6 N HCl(aq). This solution was concentrated under reduced pressure and the recovered material was dissolved into hot isopropanol to re-crystallize. Crystals were recovered by vacuum filtration, washed with a 20 isopropanol in hexane solution, and then with ether, then dried under vacuum giving 86 mg (48%) of an orange solid. LC-MS: RT=5.25 min, [M+H]+=379.0.

Workup

  1. customThe reaction vessel was sealed
  2. temperatureThe reaction was cooled to room temperature
  3. filtrationThe precipitate was recovered by vacuum filtration
  4. additiontreated with saturated NaHCO3(aq)
  5. extractionextracted three times with EtOAc
  6. washThe EtOAc extracts were washed with brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. washeluted through a 20 gram column of silica gel with 99:1:0.1 CH2Cl2
  11. dissolutionThe recovered material was dissolved into MeOH
  12. concentrationThis solution was concentrated under reduced pressure
  13. dissolutionthe recovered material was dissolved into hot isopropanol
  14. customto re-crystallize
  15. filtrationCrystals were recovered by vacuum filtration
  16. washwashed with a 20 isopropanol in hexane solution
  17. dry with materialwith ether, then dried under vacuum

Sources & evidence

ORD record
ord-1fe955d13c8d4b6a8a7126a3afef2f68
Source dataset
uspto-grants-2011_08
Patent number
US08008499B2

Reaction notes

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