Thiourea → HCID 86690852, compound

HRID 1465548Notes

Reaction equation

HRID 1465548 reaction equation
Br[CH2:2][C:3]([C:5]1[C:10]([O:11][CH3:12])=[CH:9][C:8]([F:13])=[CH:7][C:6]=1[Cl:14])=O.[NH2:15][C:16]([NH2:18])=[S:17]>CCO>[Cl:14][C:6]1[CH:7]=[C:8]([F:13])[CH:9]=[C:10]([O:11][CH3:12])[C:5]=1[C:3]1[N:15]=[C:16]([NH2:18])[S:17][CH:2]=1

Participants

4

Reactant 2

HCID 2723790ThioureaHCID 86690853HCID 86690853, compound

Product 1

HCID 86690852HCID 86690852, compoundYield 28.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2-bromo-1-(2-chloro-4-fluoro-6-methoxyphenyl)ethanone (14-1, 0.84 g) and thiourea (0.27 g, 3.6 mmol) in 95% EtOH (8.0 mL) was heated at reflux for 60 min. The solution was concentrated under reduced pressure, and the residue was re-dissolved in ethyl acetate. The solution was washed with saturated aqueous NaHCO3, dried over MgSO4, and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel to give 4-(2-chloro-4-fluoro-6-methoxyphenyl)thiazol-2-ylamine (14-2, 0.22 g, 0.85 mmol) as yellow solids in 28% yield: 1H NMR (500 MHz, CDCl3) δ 6.81 (m, 1 H), 6.60 (m, 1 H), 6.49 (s, 1 H), 3.79 (s, 3 H).

Workup

  1. temperatureat reflux for 60 min
  2. concentrationThe solution was concentrated under reduced pressure
  3. dissolutionthe residue was re-dissolved in ethyl acetate
  4. washThe solution was washed with saturated aqueous NaHCO3
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-a09ddc00926e4d1e91e931e071412526
Source dataset
uspto-grants-2015_04
Patent number
US08999983B2

Reaction notes

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