2-Bromopropiophenone → 2-Amino-4-phenyl-5-methylthiazole

HRID 1480715Notes

Reaction equation

HRID 1480715 reaction equation
Br[CH:2]([CH3:11])[C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=O.[NH2:12][C:13]([NH2:15])=[S:14]>CCO>[CH3:11][C:2]1[S:14][C:13]([NH2:15])=[N:12][C:3]=1[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 164522-BromopropiophenoneHCID 2723790Thiourea

Product 1

HCID 961292-Amino-4-phenyl-5-methylthiazoleYield 109.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-bromo-1-phenylpropan-1-one (3.00 g, 19.5 mmol) and thiourea (1.56 g, 20.5 mmol) in 95% EtOH (30 mL) was heated at reflux for 60 min. The solution was concentrated and mixed with water (100 mL) and saturated aqueous Na2CO3 (5.0 mL). The resultant precipitate was filtered and recrystallized in toluene. The solids were filtered and dried under vacuum to give 5-methyl-4-phenylthiazol-2-amine (4.07 g) as yellow solids in 77% yield: 1H NMR (500 MHz, DMSO-d6) δ 8.85 (s, 2H), 7.54-7.49 (m, 5H), 2.28 (s, 3H).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 60 min
  3. concentrationThe solution was concentrated
  4. additionmixed with water (100 mL) and saturated aqueous Na2CO3 (5.0 mL)
  5. filtrationThe resultant precipitate was filtered
  6. customrecrystallized in toluene
  7. filtrationThe solids were filtered
  8. customdried under vacuum

Sources & evidence

ORD record
ord-b82901a1909744468491512070e89d7a
Source dataset
uspto-grants-2016_08
Patent number
US09409902B2

Reaction notes

Loading…