Thiourea → HCID 58442555, compound

HRID 1843780Notes

Reaction equation

HRID 1843780 reaction equation
Br[CH2:2][C:3]([C:5]1[C:10]([CH3:11])=[CH:9][C:8]([O:12][CH2:13][CH:14]([OH:17])[CH2:15][OH:16])=[CH:7][C:6]=1[CH3:18])=O.[NH2:19][C:20]([NH2:22])=[S:21]>CCO>[NH2:22][C:20]1[S:21][CH:2]=[C:3]([C:5]2[C:10]([CH3:11])=[CH:9][C:8]([O:12][CH2:13][CH:14]([OH:17])[CH2:15][OH:16])=[CH:7][C:6]=2[CH3:18])[N:19]=1

Participants

4

Reactant 2

HCID 2723790ThioureaHCID 58442378HCID 58442378, compound

Product 1

HCID 58442555HCID 58442555, compoundYield 104.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A reaction mixture containing 2-bromo-1-(4-(2,3-dihydroxypropoxy)-2,6-dimethylphenyl)ethanone (741.9 mg, 2.3 mmol, 1.0 equiv) and thiourea (178.1 mg, 2.3 mmol, 1.0 equiv) in EtOH (10.0 mL) was heated at reflux for 16 h. The solution was concentrated under reduced pressure, and the residue was re-dissolved in EtOAc (30 mL). The solution was washed with saturated aqueous NaHCO3 (30 mL), dried over MgSO4, and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (30.0% EtOAc in hexanes as eluant) to provide 3-(4-(2-aminothiazol-4-yl)-3,5-dimethylphenoxy)propane-1,2-diol (694.1 mg, 2.4 mmol) as yellow solids in >99% yield: 1H NMR (CDCl3, 500 MHz) δ 6.76 (s, 2 H), 5.31-5.32 (m, 1 H), 3.99-4.00 (m, 1 H), 3.79-3.87 (m, 1 H), 3.78-3.79 (m, 1 H), 3.43-3.44 (m, 2 H), 3.37 (brs, 2 H), 2.15 (s, 6 H); ESI-MS: m/z 295.6 (M+H)+.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 16 h
  3. concentrationThe solution was concentrated under reduced pressure
  4. dissolutionthe residue was re-dissolved in EtOAc (30 mL)
  5. washThe solution was washed with saturated aqueous NaHCO3 (30 mL)
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by column chromatography on silica gel (30.0% EtOAc in hexanes as eluant)

Sources & evidence

ORD record
ord-e20a1110327a444d8f161d852851380f
Source dataset
uspto-grants-2015_02
Patent number
US08946268B2

Reaction notes

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