2-Bromo-1-(2,4-dimethoxyphenyl)ethanone → 4-(2,4-Dimethoxy-phenyl)-thiazol-2-ylamine

HRID 1480719Notes

Reaction equation

HRID 1480719 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][C:6]=1[O:13][CH3:14])=O.[NH2:15][C:16]([NH2:18])=[S:17]>CCO>[CH3:14][O:13][C:6]1[CH:7]=[C:8]([O:11][CH3:12])[CH:9]=[CH:10][C:5]=1[C:3]1[N:15]=[C:16]([NH2:18])[S:17][CH:2]=1

Participants

4

Reactant 2

HCID 986832-Bromo-1-(2,4-dimethoxyphenyl)ethanoneHCID 2723790Thiourea

Product 1

HCID 7452774-(2,4-Dimethoxy-phenyl)-thiazol-2-ylamineYield 82.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-bromo-1-(2,4-dimethoxyphenyl)ethanone (14.5 g, 55.8 mmol) and thiourea (4.32 g, 56.7 mmol) in 95% EtOH (110 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-(2,4-dimethoxyphenyl)thiazol-2-amine (10.9 g) as yellow solids in 62% yield: 1H NMR (500 MHz, DMSO-d6) δ 8.60 (s, 2H), 7.53 (s, 1H), 6.97 (s, 1H), 6.69 (s, 1H), 6.67-6.63 (m, 1H), 3.86 (s, 3H), 3.80 (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-5ba0f45a41b049e6b52930219ef5d604
Source dataset
uspto-grants-2016_08
Patent number
US09409902B2

Reaction notes

Loading…