2-bromo-1-(4-methoxyphenyl)propan-1-one → 4-(4-Methoxyphenyl)-5-methyl-1,3-thiazol-2(3H)-iminato

HRID 1465658Notes

Reaction equation

HRID 1465658 reaction equation
Br[CH:2]([CH3:13])[C:3]([C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][CH:6]=1)=O.[NH2:14][C:15]([NH2:17])=[S:16]>CCO>[CH3:12][O:11][C:8]1[CH:9]=[CH:10][C:5]([C:3]2[N:14]=[C:15]([NH2:17])[S:16][C:2]=2[CH3:13])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 2991022-bromo-1-(4-methoxyphenyl)propan-1-oneHCID 2723790Thiourea

Product 1

HCID 6132284-(4-Methoxyphenyl)-5-methyl-1,3-thiazol-2(3H)-iminatoYield 78%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-bromo-1-(4-methoxyphenyl)propan-1-one (10.4 g, 36.1 mmol) and thiourea (2.76 g, 36.2 mmol) in 95% EtOH (70 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 4-(4-methoxyphenyl)-5-methylthiazol-2-amine (6.16 g) as yellow solids in 78% yield: 1H NMR (500 MHz, DMSO-d6) δ 8.90 (s, 2 H), 7.46-7.44 (m, 2 H), 7.09-7.07 (m, 2 H), 3.81 (s, 3 H), 2.47 (s, 3 H).

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-9fe4a331b00146a3b547bb928b8b6e5f
Source dataset
uspto-grants-2015_04
Patent number
US08999983B2

Reaction notes

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