Thiourea → HCID 82049129, compound

HRID 1484711Notes

Reaction equation

HRID 1484711 reaction equation
Br[CH2:2][C:3]([C:5]1[C:10]([CH3:11])=[CH:9][C:8]([O:12][CH3:13])=[CH:7][C:6]=1[CH3:14])=O.[NH2:15][C:16]([NH2:18])=[S:17]>CCO>[CH3:13][O:12][C:8]1[CH:9]=[C:10]([CH3:11])[C:5]([C:3]2[N:15]=[C:16]([NH2:18])[S:17][CH:2]=2)=[C:6]([CH3:14])[CH:7]=1

Participants

4

Reactant 2

HCID 2723790ThioureaHCID 58442455HCID 58442455, compound

Product 1

HCID 82049129HCID 82049129, compoundYield 90.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The mixture of 2-bromo-1-(4-methoxy-2,6-dimethylphenyl)ethanone (160 mg, 0.62 mmol) and thiourea (61 mg, 0.80 mmol) in EtOH (4 ml) was refluxed for 45 min. After that, all the solvent was removed in vacuo and to the residue was added H2O (50 ml). The resultant solution was extracted with CH2Cl2 (3×30 mL). The combined organic phases were dried over anhydrous Na2SO4. After filtration, the solvent was removed in vacuo and the residue was purified by silica gel column (hexane/EtOAc=2/1 to 1/1) to afford 4-(4-methoxy-2,6-dimethylphenyl)thiazol-2-amine (132 mg, 90.9%) as light yellow solid. 1H NMR (500 MHz, CDCl3) δ 6.61 (s, 2H), 6.25 (s, 1H), 5.12 (br, 2H), 3.79 (s, 3H), 2.15 (s, 6H). 13C NMR (125.8 MHz, CDCl3) δ 166.7, 158.9, 149.8, 138.9, 127.9, 112.6, 105.9, 55.1, 20.6.

Workup

  1. temperaturewas refluxed for 45 min
  2. customAfter that, all the solvent was removed in vacuo and to the residue
  3. additionwas added H2O (50 ml)
  4. extractionThe resultant solution was extracted with CH2Cl2 (3×30 mL)
  5. dry with materialThe combined organic phases were dried over anhydrous Na2SO4
  6. filtrationAfter filtration
  7. customthe solvent was removed in vacuo
  8. customthe residue was purified by silica gel column (hexane/EtOAc=2/1 to 1/1)

Sources & evidence

ORD record
ord-9bb8a2c54dd24e5cb1a2ffcbc5d82616
Source dataset
uspto-grants-2016_08
Patent number
US09422275B2

Reaction notes

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