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

HRID 1465661Notes

Reaction equation

HRID 1465661 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, 2 H), 7.53 (s, 1 H), 6.97 (s, 1 H), 6.69 (s, 1 H), 6.67-6.63 (m, 1 H), 3.86 (s, 3 H), 3.80 (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-cbfbec7299984e6e9e50c51b3cc3a8f9
Source dataset
uspto-grants-2015_04
Patent number
US08999983B2

Reaction notes

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