2-Bromo-4'-methylacetophenone → 4-(4-Methylphenyl)-1,3-thiazol-2(3H)-imine

HRID 1480652Notes

Reaction equation

HRID 1480652 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([CH3:11])=[CH:7][CH:6]=1)=O.[NH2:12][C:13]([NH2:15])=[S:14]>CCO>[C:8]1([CH3:11])[CH:9]=[CH:10][C:5]([C:3]2[N:12]=[C:13]([NH2:15])[S:14][CH:2]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 692722-Bromo-4'-methylacetophenoneHCID 2723790Thiourea

Product 1

HCID 2440664-(4-Methylphenyl)-1,3-thiazol-2(3H)-imineYield 99%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-bromo-1-(p-tolyl)ethanone (5.00 g, 23.5 mmol) and thiourea (1.97 g, 25.9 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 (1.0 mL). The resultant precipitate was filtered and washed with hot water. The solids were filtered and dried under vacuum to give 4-(p-tolyl)thiazol-2-amine (4.40 g) as white solids in 99% yield: 1H NMR (500 MHz, CDCl3) δ 7.66 (d, J=8.0 Hz, 2H), 7.18 (d, J=7.5 Hz, 2H), 6.66 (s, 1H), 5.25 (bs, 2H), 2.36 (s, 6H).

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 (1.0 mL)
  5. filtrationThe resultant precipitate was filtered
  6. washwashed with hot water
  7. filtrationThe solids were filtered
  8. customdried under vacuum

Sources & evidence

ORD record
ord-30528c9c3631407ea3a7613df4b66546
Source dataset
uspto-grants-2016_08
Patent number
US09409902B2

Reaction notes

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