Thiourea → HCID 82049129, compound

HRID 1480655Notes

Reaction equation

HRID 1480655 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 74.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-bromo-1-(4-methoxy-2,6-dimethylphenyl)ethanone (8.65 g, 33.6 mmol) and thiourea (2.56 g, 33.6 mmol) in 95% EtOH (48 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 (50 mL). The solids were filtered and dried under vacuum to give 4-(4-methoxy-2,6-dimethylphenyl)thiazol-2-amine (5.9 g) as white solids in 66% yield: 1H NMR (500 MHz, CDCl3) δ 6.61 (s, 2H), 6.27 (s, 1H), 4.91 (bs, 2H), 3.79 (s, 3H), 2.15 (s, 6H).

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 (50 mL)
  7. filtrationThe solids were filtered
  8. customdried under vacuum

Sources & evidence

ORD record
ord-fbb8c2e9ebed4a9fb56a5b2852f9305a
Source dataset
uspto-grants-2016_08
Patent number
US09409902B2

Reaction notes

Loading…