Sodium Bicarbonate → HCID 58026093, compound

HRID 1843776Notes

Reaction equation

HRID 1843776 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, 2 H), 7.12-7.14 (m, 3 H), 3.92 (s, 3 H); 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-ceb42184461e43878ac3ea25f4531963
Source dataset
uspto-grants-2015_02
Patent number
US08946268B2

Reaction notes

Loading…