Thiourea → HCID 58442459, compound

HRID 1843759Notes

Reaction equation

HRID 1843759 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, 4 H), 6.66 (s, 2 H), 6.28 (s, 1 H), 5.95 (bs, 2 H), 2.14 (s, 6 H).

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-a24753d0eeb34644b30278655b1ec0ad
Source dataset
uspto-grants-2015_02
Patent number
US08946268B2

Reaction notes

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