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

HRID 1480653Notes

Reaction equation

HRID 1480653 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 solids 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, 2H), 7.23 (d, J=8.0 Hz, 2H), 3.18 (bs, 2H), 2.37 (s, 3H), 2.35 (s, 3H).

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 solids were filtered
  8. customdried under vacuum

Sources & evidence

ORD record
ord-40597f35da2d46b0ba21a98a7b235e02
Source dataset
uspto-grants-2016_08
Patent number
US09409902B2

Reaction notes

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