Thiourea → 5-(4-Methoxy-benzyl)-thiazol-2-ylamine

HRID 333914Notes

Reaction equation

HRID 333914 reaction equation
Br[CH:2]([CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[CH:8][CH:7]=1)[CH:3]=O.[NH2:14][C:15]([NH2:17])=[S:16]>CCO>[CH3:13][O:12][C:9]1[CH:10]=[CH:11][C:6]([CH2:5][C:2]2[S:16][C:15]([NH2:17])=[N:14][CH:3]=2)=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 2723790ThioureaHCID 25000328HCID 25000328, compound

Product 1

HCID 31330525-(4-Methoxy-benzyl)-thiazol-2-ylamineYield 75.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-bromo-3-(4-methoxy-phenyl)-propionaldehyde (9c) and thiourea (0.84 g, 11.0 mmol) in 95% EtOH (20.0 mL) was heated at reflux for 60 minutes. The solution was concentrated under reduced pressure and the residue was re-dissolved in ethyl acetate. The solution was washed with saturated aqueous NaHCO3, dried over MgSO4(s), and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel to give 5-(4-methoxy-benzyl)-thiazol-2-ylamine (9d, 1.01 g, 4.54 mmol) as yellow solids in 75.2% yield.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 60 minutes
  3. concentrationThe solution was concentrated under reduced pressure
  4. dissolutionthe residue was re-dissolved in ethyl acetate
  5. washThe solution was washed with saturated aqueous NaHCO3
  6. dry with materialdried over MgSO4(s)
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-67cf435189124411a925991e0532d451
Source dataset
uspto-grants-2014_11
Patent number
US08883793B2

Reaction notes

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