p-Toluenesulfonic acid → HCID 15205159, compound

HRID 868988Notes

Reaction equation

HRID 868988 reaction equation
[CH3:1][N:2]1[CH:6]=[CH:5][N:4]=[C:3]1[CH:7]=[O:8].CC1C=CC(S(O)(=O)=O)=[CH:14][CH:15]=1.C(=O)(O)[O-:21].[Na+]>C1(C)C=CC=CC=1>[O:8]1[CH2:15][CH2:14][O:21][CH:7]1[C:3]1[N:2]([CH3:1])[CH:6]=[CH:5][N:4]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 1395751-Methyl-2-imidazolecarboxaldehydeHCID 516892Sodium Bicarbonate

Product 1

HCID 15205159HCID 15205159, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 1-methyl-1H-imidazole-2-carbaldehyde (24 g, 218 mmol), p-TsOH (16.2 g, 87 mmol), glycol (27 g, 437 mmol), and toluene (700 mL) was heated to 120° C. in a Dean-Stark apparatus for 16 h. Then the mixture was cooled to room temperature, pH was adjusted to 9 with saturated sodium bicarbonate solution at 0° C., and the mixture was extracted with EtOAc (500 mL×2). The organic layers were washed with water (200 mL) and brine (100 mL), dried, filtered, then concentrated to give a red oil (12 g). MS (ESI): m/z 155.1 [M+H]+.

Workup

  1. temperatureThen the mixture was cooled to room temperature
  2. extractionthe mixture was extracted with EtOAc (500 mL×2)
  3. washThe organic layers were washed with water (200 mL) and brine (100 mL)
  4. customdried
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-f8bad1c5a11f4d93a8b5f3947d296eb2
Source dataset
uspto-grants-2015_03
Patent number
US08969349B2

Reaction notes

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