Thiourea → HCID 58442508, compound

HRID 1843743Notes

Reaction equation

HRID 1843743 reaction equation
Br[CH2:2][C:3]([C:5]1[C:10]([CH3:11])=[CH:9][C:8]([Cl:12])=[CH:7][C:6]=1[CH3:13])=O.[NH2:14][C:15]([NH2:17])=[S:16]>CCO>[Cl:12][C:8]1[CH:9]=[C:10]([CH3:11])[C:5]([C:3]2[N:14]=[C:15]([NH2:17])[S:16][CH:2]=2)=[C:6]([CH3:13])[CH:7]=1

Participants

4

Reactant 2

HCID 2723790ThioureaHCID 58442377HCID 58442377, compound

Product 1

HCID 58442508HCID 58442508, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-bromo-1-(4-chloro-2,6-dimethylphenyl)ethanone (6.54 g, 25.0 mmol) and thiourea (1.90 g, 25.0 mmol) in 95% EtOH (35.7 mL) was heated at reflux for 60 min. The solution was concentrated and added with water (50 mL) followed by saturated aqueous Na2CO3 (4.0 mL). The resultant precipitate was filtered and recrystallized in toluene (30 mL). The solids were filtered and dried under vacuum to give 4-(4-chloro-2,6-dimethylphenyl)thiazol-2-amine (4.30 g) as white solids in 72% yield: 1H NMR (500 MHz, DMSO-d6) δ 7.16 (s, 2 H), 6.43 (s, 1 H), 2.10 (s, 6 H).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 60 min
  3. concentrationThe solution was concentrated
  4. additionadded with water (50 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-61139ffa1fe6408a979590ad28013401
Source dataset
uspto-grants-2015_02
Patent number
US08946268B2

Reaction notes

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