Thiourea → HCID 86690849, compound

HRID 1465546Notes

Reaction equation

HRID 1465546 reaction equation
Br[CH2:2][C:3]([C:5]1[C:10]([F:11])=[CH:9][C:8]([O:12][CH3:13])=[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]([O:12][CH3:13])[CH:9]=[C:10]([F:11])[C:5]=1[C:3]1[N:15]=[C:16]([NH2:18])[S:17][CH:2]=1

Participants

4

Reactant 2

HCID 2723790ThioureaHCID 86690850HCID 86690850, compound

Product 1

HCID 86690849HCID 86690849, compoundYield 42.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2-bromo-1-(2-chloro-6-fluoro-4-methoxyphenyl)ethanone (13-4, 0.80 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-6-fluoro-4-methoxyphenyl)thiazol-2-ylamine (13-5, 0.30 g, 1.2 mmol) as yellow solids in 39% yield: 1H NMR (500 MHz, CDCl3) δ 6.84 (s, 1 H), 6.65 (m, 1 H), 6.57 (s, 1 H), 3.83 (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-5000d0f0390d45898f43fd7df26dea99
Source dataset
uspto-grants-2015_04
Patent number
US08999983B2

Reaction notes

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