Thiourea → HCID 58442527, compound

HRID 1843760Notes

Reaction equation

HRID 1843760 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, 1 H), 3.70 (d, J=6.5 Hz, 2 H), 2.15 (s, 6 H), 2.07 (m, 1 H), 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-e2a98ee5d0ff42558986793c920e37ee
Source dataset
uspto-grants-2015_02
Patent number
US08946268B2

Reaction notes

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