2-Bromo-1-mesitylethanone → 4-(2,4,6-Trimethylphenyl)-1,3-thiazol-2-amine

HRID 1843729Notes

Reaction equation

HRID 1843729 reaction equation
Br[CH2:2][C:3]([C:5]1[C:10]([CH3:11])=[CH:9][C:8]([CH3:12])=[CH:7][C:6]=1[CH3:13])=O.[NH2:14][C:15]([NH2:17])=[S:16]>C(O)C>[C:6]1([CH3:13])[CH:7]=[C:8]([CH3:12])[CH:9]=[C:10]([CH3:11])[C:5]=1[C:3]1[N:14]=[C:15]([NH2:17])[S:16][CH:2]=1

Participants

4

Reactant 2

HCID 2194802-Bromo-1-mesitylethanoneHCID 2723790Thiourea

Product 1

HCID 6127164-(2,4,6-Trimethylphenyl)-1,3-thiazol-2-amineYield 107%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-Bromo-1-mesitylethanone (2.43 g, 10.1 mmol) and thiourea (0.810 g, 10.6 mmol) were dissolved in 95% ethanol (20 mL). The reaction mixture was heated at reflux for 2.0 h. The solution was concentrated under reduced pressure, and the residue was recrystallized from 2-propanol to give the desired 4-mesitylthiazol-2-amine (2.36 g) as white solids: 1H NMR (500 MHz, CD3OD) δ 7.00 (2 H, s), 6.67 (1 H, s), 2.31 (3 H, s), 2.19 (6 H, s).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 2.0 h
  3. concentrationThe solution was concentrated under reduced pressure
  4. customthe residue was recrystallized from 2-propanol

Sources & evidence

ORD record
ord-eca3dc64c5f541a2af613db45b04ada9
Source dataset
uspto-grants-2015_02
Patent number
US08946268B2

Reaction notes

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