Thiourea → HCID 58442525, compound

HRID 1843754Notes

Reaction equation

HRID 1843754 reaction equation
Br[CH2:2][C:3]([C:5]1[C:10]([CH3:11])=[CH:9][C:8]([O:12][CH:13]2[CH2:17][CH2:16][CH2:15][CH2:14]2)=[CH:7][C:6]=1[CH3:18])=O.[NH2:19][C:20]([NH2:22])=[S:21]>CCO>[CH:13]1([O:12][C:8]2[CH:9]=[C:10]([CH3:11])[C:5]([C:3]3[N:19]=[C:20]([NH2:22])[S:21][CH:2]=3)=[C:6]([CH3:18])[CH:7]=2)[CH2:17][CH2:16][CH2:15][CH2:14]1

Participants

4

Reactant 2

HCID 2723790ThioureaHCID 58442422HCID 58442422, compound

Product 1

HCID 58442525HCID 58442525, compoundYield 73.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-bromo-1-(4-(cyclopentyloxy)-2,6-dimethylphenyl)ethanone (6.16 g, 19.8 mmol) and thiourea (1.51 g, 19.8 mmol) in 95% EtOH (28.3 mL) was heated at reflux for 90 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-(cyclopentyloxy)-2,6-dimethylphenyl)thiazol-2-amine (4.2 g) as white solids in 73.7% yield: 1H NMR (500 MHz, CDCl3) δ 6.58 (s, 2 H), 6.24 (s, 1 H), 4.75 (m, 1 H), 2.13 (s, 6 H), 1.88-1.78 (m, 6 H), 1.62-1.59 (m, 2 H).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 90 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-686effc6ef6440a9938b56ded3a49278
Source dataset
uspto-grants-2015_02
Patent number
US08946268B2

Reaction notes

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