Pyridine → HCID 54264787, compound

HRID 1741984Notes

Reaction equation

HRID 1741984 reaction equation
N1C=CC=CC=1.C(O)(C(F)(F)F)=O.[CH3:14][O:15][CH2:16][CH2:17][O:18][CH2:19][O:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][OH:30].C1(N=C=NC2CCCCC2)CCCCC1>C1C=CC=CC=1.CS(C)=O>[CH3:14][O:15][CH2:16][CH2:17][O:18][CH2:19][O:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH:29]=[O:30]

Participants

6

Reactant 4

HCID 1049PyridineHCID 6422Trifluoroacetic acidHCID 10868DicyclohexylcarbodiimideHCID 54286532HCID 54286532, compound

Product 1

HCID 54264787HCID 54264787, compound

Reagents, catalysts & solvents 1

HCID 18518713Benzene dimethylsulfoxideSolvent2×

Procedure

About 5 ml of the solvent mixture benzene/DMSO (1:1) are introduced into a two-neck flask which has been flame-treated and flushed with nitrogen, and 1 mmol of absolute pyridine and 0.5 mmol of CF3COOH, and 1 mmol of 1 and 3 mmol of dicyclohexylcarbodiimide (DCCI), dissolved in benzene/DMSO, are added with stirring. The mixture is stirred overnight at room temperature. Precipitated dicyclohexylurea is filtered off, and the solution is evaporated on a rotary evaporator. DMSO is removed by repeated shaking with water and, if necessary, at 40° C. in a bulb tube. The crude product is filtered again and purified by flash chromatography (PE/CH2Cl2).

Workup

  1. additionhas been flame-treated
  2. additionare added
  3. stirringThe mixture is stirred overnight at room temperature
  4. filtrationPrecipitated dicyclohexylurea is filtered off
  5. customthe solution is evaporated on a rotary evaporator
  6. customDMSO is removed
  7. stirringby repeated shaking with water
  8. customat 40° C.
  9. filtrationThe crude product is filtered again
  10. custompurified by flash chromatography (PE/CH2Cl2)

Sources & evidence

ORD record
ord-b8ce5c067b464a50bbb87e765696e0c1
Source dataset
uspto-grants-1994_08
Patent number
US05336436

Reaction notes

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