Thiourea → 4-(2-Aminothiazol-4-yl)-3,5-dimethylphenol

HRID 1465524Notes

Reaction equation

HRID 1465524 reaction equation
Br[CH2:2][C:3]([C:5]1[C:10]([CH3:11])=[CH:9][C:8]([OH:12])=[CH:7][C:6]=1[CH3:13])=O.[NH2:14][C:15]([NH2:17])=[S:16]>CCO>[NH2:17][C:15]1[S:16][CH:2]=[C:3]([C:5]2[C:10]([CH3:11])=[CH:9][C:8]([OH:12])=[CH:7][C:6]=2[CH3:13])[N:14]=1

Participants

4

Reactant 2

HCID 2723790ThioureaHCID 826327342-Bromo-1-(4-hydroxy-2,6-dimethylphenyl)ethanone

Product 1

HCID 866908264-(2-Aminothiazol-4-yl)-3,5-dimethylphenolYield 79%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-bromo-1-(4-hydroxy-2,6-dimethylphenyl)ethanone (5-1, 2.43 g, 10.0 mmol) and thiourea (1.37 g, 18.0 mmol) in 95% EtOH (30 mL) was heated at reflux for 120 min. The solution was concentrated and added with water (50 mL) and saturated aqueous Na2CO3 (5.0 mL). The resultant precipitate was filtered and washed with a solution of 50% EtOAc in hexanes. The solids were dried under vacuum to give 4-(2-aminothiazol-4-yl)-3,5-dimethylphenol (5-2, 1.74 g) as pale yellow solids in 79% yield: 1H NMR (500 MHz, CDCl3) δ 8.7 (s, 2 H), 6.17 (s, 2 H), 5.97 (s, 1 H), 1.71 (s, 6 H).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 120 min
  3. concentrationThe solution was concentrated
  4. additionadded with water (50 mL) and saturated aqueous Na2CO3 (5.0 mL)
  5. filtrationThe resultant precipitate was filtered
  6. washwashed with a solution of 50% EtOAc in hexanes
  7. customThe solids were dried under vacuum

Sources & evidence

ORD record
ord-8b590fbde916412281314a91b3df24c9
Source dataset
uspto-grants-2015_04
Patent number
US08999983B2

Reaction notes

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