Thiourea → HCID 58442527, compound

HRID 1465624Notes

Reaction equation

HRID 1465624 reaction equation
Br[CH2:2][C:3]([C:5]1[C:10]([CH3:11])=[CH:9][C:8]([O:12][CH2:13][CH:14]([CH3:16])[CH3:15])=[CH:7][C:6]=1[CH3:17])=O.[NH2:18][C:19]([NH2:21])=[S:20]>CCO>[CH2:13]([O:12][C:8]1[CH:9]=[C:10]([CH3:11])[C:5]([C:3]2[N:18]=[C:19]([NH2:21])[S:20][CH:2]=2)=[C:6]([CH3:17])[CH:7]=1)[CH:14]([CH3:16])[CH3:15]

Participants

4

Reactant 2

HCID 2723790ThioureaHCID 58442375HCID 58442375, compound

Product 1

HCID 58442527HCID 58442527, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-bromo-1-(4-isobutoxy-2,6-dimethylphenyl)ethanone (5.84 g, 19.5 mmol) and thiourea (1.49 g, 19.6 mmol) in 95% EtOH (28 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-isobutoxy-2,6-dimethylphenyl)thiazol-2-amine (4.4 g) as white solids in 82% yield: 1H NMR (500 MHz, CDCl3) δ 6.61 (s, 2 H), 6.24 (s, 1H), 3.70 (d, J=6.5 Hz, 2 H), 2.15 (s, 6 H), 2.07 (m, 1H), 1.01 (d, J=6.7 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-2e60a417aa394c9aa79c1c1de7202f94
Source dataset
uspto-grants-2015_04
Patent number
US08999983B2

Reaction notes

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