Thiourea → HCID 58442444, compound

HRID 1465601Notes

Reaction equation

HRID 1465601 reaction equation
Br[CH2:2][C:3]([C:5]1[C:10]([CH3:11])=[CH:9][C:8]([O:12][CH2:13][CH3:14])=[CH:7][C:6]=1[CH3:15])=O.[NH2:16][C:17]([NH2:19])=[S:18]>CCO>[CH2:13]([O:12][C:8]1[CH:9]=[C:10]([CH3:11])[C:5]([C:3]2[N:16]=[C:17]([NH2:19])[S:18][CH:2]=2)=[C:6]([CH3:15])[CH:7]=1)[CH3:14]

Participants

4

Reactant 2

HCID 2723790ThioureaHCID 58442385HCID 58442385, compound

Product 1

HCID 58442444HCID 58442444, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-bromo-1-(4-ethoxy-2,6-dimethylphenyl)ethanone (6.35 g, 23.4 mmol) and thiourea (1.78 g, 23.4 mmol) in 95% EtOH (33.5 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-ethoxy-2,6-dimethylphenyl)thiazol-2-amine (4.18 g) as white solids in 72% yield: 1H NMR (500 MHz, DMSO-d6) δ 6.84 (s, 2 H), 6.60 (s, 2 H), 6.27 (s, 1 H), 3.99 (q, J=6.5 Hz, 2 H), 2.06 (s, 6 H), 1.31 (t, J=6.95 Hz, 3 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-bf4244646b1f421fa0d349f8324835d1
Source dataset
uspto-grants-2015_04
Patent number
US08999983B2

Reaction notes

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