Bromine → 4-(2',4'-Dichlorophenyl)-5-methylthiazole hydrobromide

HRID 1729272Notes

Reaction equation

HRID 1729272 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9](=O)[CH2:10][CH3:11].[Br:13]Br.[CH:15]([NH2:17])=[S:16]>C(Cl)Cl>[BrH:13].[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[N:17]=[CH:15][S:16][C:10]=1[CH3:11]

Participants

5

Reactant 3

HCID 24408BromineHCID 1234672',4'-DichloropropiophenoneHCID 3005587Methanethioamide

Product 1

HCID 190124704-(2',4'-Dichlorophenyl)-5-methylthiazole hydrobromideYield 53%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
20 °C

Procedure

To 2',4'-dichloropropiophenone (2.03 g; 0.01 mole) in methylene chloride (20 ml) was added excess bromine in methylene chloride (10 ml) dropwise at 20° C. The methylene chloride layer was washed with sodium sulphite solution and water, separated, dried (MgSO4) and evaporated. The residue was dissolved in ethanol (20 ml) and thioformamide (0.61 g; 0.01 mole) was added and the mixture stirred at 20° C. for 16 hours to give 4-(2',4'-dichlorophenyl)-5-methylthiazole hydrobromide (1.72 g; 53%).

Workup

  1. washThe methylene chloride layer was washed with sodium sulphite solution and water
  2. customseparated
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. dissolutionThe residue was dissolved in ethanol (20 ml)

Sources & evidence

ORD record
ord-710cdbd9ed75436bbc898ae53e73aa5c
Source dataset
uspto-grants-1994_07
Patent number
US05332753

Reaction notes

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