Hydrochloric Acid → HCID 178490772, compound

HRID 1893712Notes

Reaction equation

HRID 1893712 reaction equation
[CH3:1][O:2][C:3]1[CH:21]=[CH:20][C:6]([CH2:7][N:8]2[CH:12]=[C:11]([C:13](=O)[CH2:14][S:15][C:16]#[N:17])[C:10]([CH3:19])=[N:9]2)=[CH:5][CH:4]=1.Cl.CC[OH:25]>>[CH3:1][O:2][C:3]1[CH:21]=[CH:20][C:6]([CH2:7][N:8]2[CH:12]=[C:11]([C:13]3[N:17]=[C:16]([OH:25])[S:15][CH:14]=3)[C:10]([CH3:19])=[N:9]2)=[CH:5][CH:4]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 86665171HCID 86665171, compound

Product 1

HCID 178490772HCID 178490772, compoundYield 52%

Procedure

According to Scheme 2, Step 4: To a solution of 1-(1-(4-methoxybenzyl)-3-methyl-1H-pyrazol-4-yl)-2-thiocyanatoethanone (6.57 mmol, 1.98 g) in EtOH was added HCl concentrated (1 mL) and the reaction mixture was stirred under reflux for 8 hours. After cooling to room temperature, the solvent was removed under reduced pressure and the residue was diluted with water. The aqueous phase was basified with NaOH and was extracted with DCM. The organic phase was dried over MgSO4, was filtered and was evaporated. The crude residue was purified by flash chromatography over silica gel using DCM/EtOH/NH3 (100:0:0 to 95:4.5:0.5) as eluent to yield 4-(1-(4-methoxybenzyl)-3-methyl-1H-pyrazol-4-yl)thiazol-2-ol (3.42 mmol, 1.03 g, 52%).

Workup

  1. concentrationconcentrated (1 mL)
  2. temperatureunder reflux for 8 hours
  3. customthe solvent was removed under reduced pressure
  4. additionthe residue was diluted with water
  5. extractionwas extracted with DCM
  6. dry with materialThe organic phase was dried over MgSO4
  7. filtrationwas filtered
  8. customwas evaporated
  9. customThe crude residue was purified by flash chromatography over silica gel

Sources & evidence

ORD record
ord-009a6b999f1a45fd9c6dc805acbc99d7
Source dataset
uspto-grants-2013_08
Patent number
US08513252B2

Reaction notes

Loading…