Thiourea → 5-methyl-4-(4-methylphenyl)-1,3-thiazol-2-amine

HRID 1465595Notes

Reaction equation

HRID 1465595 reaction equation
Br[CH:2]([CH3:12])[C:3]([C:5]1[CH:10]=[CH:9][C:8]([CH3:11])=[CH:7][CH:6]=1)=O.[NH2:13][C:14]([NH2:16])=[S:15]>CCO>[CH3:12][C:2]1[S:15][C:14]([NH2:16])=[N:13][C:3]=1[C:5]1[CH:10]=[CH:9][C:8]([CH3:11])=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 2723790ThioureaHCID 27340632-Bromo-1-(4-methylphenyl)propan-1-one

Product 1

HCID 7022655-methyl-4-(4-methylphenyl)-1,3-thiazol-2-amineYield 99%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-bromo-1-(p-tolyl)propan-1-one (6.88 g, 30.3 mmol) and thiourea (2.54 g, 33.4 mmol) in 95% EtOH (43 mL) was heated at reflux for 60 min. The solution was concentrated and added with water (100 mL) and saturated aqueous Na2CO3 (5.0 mL). The resultant precipitate was filtered and recrystallized in toluene. The solid were filtered and dried under vacuum to give 5-methyl-4-(p-tolyl)thiazol-2-amine (6.10 g) as white solids in 99% yield: 1H NMR (500 MHz, CDCl3) δ 7.40 (d, J=8.0 Hz, 2 H), 7.23 (d, J=8.0 Hz, 2 H), 3.18 (s, 2 H), 2.37 (s, 3 H), 2.35 (s, 3 H).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 60 min
  3. concentrationThe solution was concentrated
  4. additionadded with water (100 mL) and saturated aqueous Na2CO3 (5.0 mL)
  5. filtrationThe resultant precipitate was filtered
  6. customrecrystallized in toluene
  7. filtrationThe solid were filtered
  8. customdried under vacuum

Sources & evidence

ORD record
ord-34e8d412e920441eb58e8c5f079b7870
Source dataset
uspto-grants-2015_04
Patent number
US08999983B2

Reaction notes

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