Sodium Bicarbonate → HCID 58026093, compound

HRID 1480698Notes

Reaction equation

HRID 1480698 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[C:9]([F:11])[C:8]([O:12][CH3:13])=[C:7]([F:14])[CH:6]=1)=O.[NH2:15][C:16]([NH2:18])=[S:17].C([O-])(O)=O.[Na+]>CCO>[F:14][C:7]1[CH:6]=[C:5]([C:3]2[N:15]=[C:16]([NH2:18])[S:17][CH:2]=2)[CH:10]=[C:9]([F:11])[C:8]=1[O:12][CH3:13]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 2723790ThioureaHCID 21958935HCID 21958935, compound

Product 1

HCID 58026093HCID 58026093, compoundYield 85.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A reaction mixture containing 2-bromo-1-(3,5-difluoro-4-methoxyphenyl)ethanone (2.0 g, 7.5 mmol, 1.0 equiv) and thiourea (0.57 g, 7.5 mmol, 1.0 equiv) in EtOH (20.0 mL) was heated at reflux for 3.0 h. The residue was basified with saturated aqueous NaHCO3 (20 mL) and extracted with EtOAc (3×30 mL). The organic layer was separated, dried over MgSO4(s), and concentrated under reduced pressure. The resultant solids were washed with hexanes to give 4-(3,5-difluoro-4-methoxyphenyl)thiazol-2-amine (1.54 g, 6.4 mmol) as white solids in 84% yield: 1H NMR (DMSO-d6, 500 MHz) δ 7.49-7.54 (m, 2H), 7.12-7.14 (m, 3H), 3.92 (s, 3H); ESI-MS: m/z 243.0 (M+H)+.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 3.0 h
  3. extractionextracted with EtOAc (3×30 mL)
  4. customThe organic layer was separated
  5. dry with materialdried over MgSO4(s)
  6. concentrationconcentrated under reduced pressure
  7. washThe resultant solids were washed with hexanes

Sources & evidence

ORD record
ord-05fa5b24fada44868ba5446685be96ef
Source dataset
uspto-grants-2016_08
Patent number
US09409902B2

Reaction notes

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