Thiourea → HCID 58442459, compound

HRID 1480681Notes

Reaction equation

HRID 1480681 reaction equation
Br[CH2:2][C:3]([C:5]1[C:10]([CH3:11])=[CH:9][C:8]([O:12][C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)=[CH:7][C:6]=1[CH3:20])=O.[NH2:21][C:22]([NH2:24])=[S:23]>CCO>[F:19][C:16]1[CH:17]=[CH:18][C:13]([O:12][C:8]2[CH:9]=[C:10]([CH3:11])[C:5]([C:3]3[N:21]=[C:22]([NH2:24])[S:23][CH:2]=3)=[C:6]([CH3:20])[CH:7]=2)=[CH:14][CH:15]=1

Participants

4

Reactant 2

HCID 2723790ThioureaHCID 58442384HCID 58442384, compound

Product 1

HCID 58442459HCID 58442459, compoundYield 84.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-bromo-1-(4-(4-fluorophenoxy)-2,6-dimethylphenyl)ethanone (5.74 g, 17.0 mmol) and thiourea (1.30 g, 17.1 mmol) in 95% EtOH (24.3 mL) was heated at reflux for 60 min. The solution was concentrated and added with water (100 mL) and saturated aqueous Na2CO3 (5.0 mL). The resultant precipitate was filtered and recrystallized in toluene. The solids were filtered and dried under vacuum to give 4-(4-(4-fluorophenoxy)-2,6-dimethylphenyl)thiazol-2-amine (4.50 g) as yellow solids in 84% yield: 1H NMR (500 MHz, CDCl3) δ 7.05-6.97 (m, 4H), 6.66 (s, 2H), 6.28 (s, 1H), 5.95 (bs, 2H), 2.14 (s, 6H).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 60 min
  3. concentrationThe solution was concentrated
  4. additionadded with water (100 mL) and saturated aqueous Na2CO3 (5.0 mL)
  5. filtrationThe resultant precipitate was filtered
  6. customrecrystallized in toluene
  7. filtrationThe solids were filtered
  8. customdried under vacuum

Sources & evidence

ORD record
ord-c05ad1ee368e44b784f254914621dc87
Source dataset
uspto-grants-2016_08
Patent number
US09409902B2

Reaction notes

Loading…