Hydrochloric Acid → 5-(5-Ethyl-[1,2,4]oxadiazol-3-yl)-4-phenyl-thiazol-2-ylamine

HRID 604487Notes

Reaction equation

HRID 604487 reaction equation
[CH2:1]([C:3]1[O:7][N:6]=[C:5]([C:8]2[S:12][C:11]([NH:13]C(=O)CC)=[N:10][C:9]=2[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[N:4]=1)[CH3:2].Cl.C([O-])(O)=O.[Na+]>CO>[CH2:1]([C:3]1[O:7][N:6]=[C:5]([C:8]2[S:12][C:11]([NH2:13])=[N:10][C:9]=2[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[N:4]=1)[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 57709613N-[5-(5-Ethyl-[1,2,4]oxadiazol-3-yl)-4-phenyl-thiazol-2-yl]-propionamide

Product 1

HCID 577096015-(5-Ethyl-[1,2,4]oxadiazol-3-yl)-4-phenyl-thiazol-2-ylamineYield 91%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

N-[5-(5-Ethyl-[1,2,4]oxadiazol-3-yl)-4-phenyl-thiazol-2-yl]-propionamide (1.02 g, 3.1 mmol) was suspended in MeOH (40 mL), konc. HCl(aq) was added and the reaction mixture was heated at refluc for 2 h. Saturated aqueous NaHCO3 (100 mL) was added to the reaction mixture. The aqueous phase was extracted with ethyl acetate (2×75 mL). The organic phase was dried with MgSO4 and the solvent was evaporated to yield white solid. Yield: 91%.

Workup

  1. temperaturethe reaction mixture was heated at refluc for 2 h
  2. extractionThe aqueous phase was extracted with ethyl acetate (2×75 mL)
  3. dry with materialThe organic phase was dried with MgSO4
  4. customthe solvent was evaporated
  5. customto yield white solid

Sources & evidence

ORD record
ord-3a5c4291c5504297a58e9f42775811b1
Source dataset
uspto-grants-2011_03
Patent number
US07910613B2

Reaction notes

Loading…