Thiourea → HCID 58442550, compound

HRID 1843752Notes

Reaction equation

HRID 1843752 reaction equation
Br[CH2:2][C:3]([C:5]1[C:10]([CH3:11])=[CH:9][C:8]([O:12][CH:13]([CH3:15])[CH3:14])=[CH:7][C:6]=1[CH3:16])=O.[NH2:17][C:18]([NH2:20])=[S:19]>CCO>[CH:13]([O:12][C:8]1[CH:9]=[C:10]([CH3:11])[C:5]([C:3]2[N:17]=[C:18]([NH2:20])[S:19][CH:2]=2)=[C:6]([CH3:16])[CH:7]=1)([CH3:15])[CH3:14]

Participants

4

Reactant 2

HCID 2723790ThioureaHCID 58442512HCID 58442512, compound

Product 1

HCID 58442550HCID 58442550, compoundYield 72.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-bromo-1-(4-isopropoxy-2,6-dimethylphenyl)ethanone (5.18 g, 18.2 mmol) and thiourea (1.38 g, 18.2 mmol) in 95% EtOH (26 mL) was heated at reflux for 60 min. The solution was concentrated and added with water (50 mL) and saturated aqueous Na2CO3 (5.0 mL). The resultant precipitate was filtered and recrystallized in toluene (30 mL). The solids were filtered and dried under vacuum to give 4-(4-isopropoxy-2,6-dimethylphenyl)thiazol-2-amine (3.44 g) as yellow solids in 72.2% yield: 1H NMR (500 MHz, CDCl3) δ 6.60 (s, 2 H), 6.26 (s, 1 H), 4.97 (bs, 2 H), 4.54 (m, 1 H), 2.13 (s, 6 H), 1.32 (d, J=6.1 Hz, 6 H).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 60 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. customrecrystallized in toluene (30 mL)
  7. filtrationThe solids were filtered
  8. customdried under vacuum

Sources & evidence

ORD record
ord-69f7cbfc9c8c4e54b023af97d3f3cbd8
Source dataset
uspto-grants-2015_02
Patent number
US08946268B2

Reaction notes

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