N-bromobutanimide → HCID 22625625, compound

HRID 277663Notes

Reaction equation

HRID 277663 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[N:10]=[C:11]2[N:15]([CH:16]=1)[CH2:14][CH2:13][S:12]2.[Br:17]N1C(=O)CCC1=O>CN(C)C=O.O>[Br:17][C:16]1[N:15]2[C:11]([S:12][CH2:13][CH2:14]2)=[N:10][C:9]=1[C:3]1[CH:4]=[CH:5][C:6]([Cl:8])=[CH:7][C:2]=1[Cl:1]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 141451006-(2,4-Dichlorophenyl)-2,3-dihydroimidazo[2,1-b]thiazole

Product 1

HCID 22625625HCID 22625625, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

The 6-(2,4-dichlorophenyl)-2,3-dihydroimidazo[2,1-b]thiazole (0.6 g) prepared above and N-bromosuccinimide (0.45 g) were dissolved in dimethylformamide (5 ml). The mixture was heated to reflux and stirred for 18 h at room temperature. The mixture was diluted with water (60 ml) and allowed to crystallize. The liquid was decanted and the residue was dissolved in methylene chloride and dried with magnesium sulfate. The organic residue was chromatographed on silica gel with hexanes/ethyl acetate (3:1) as eluent to give the desired product as a solid (m.p. 200-202° C.); NMR (CDCl3, 200 MHz) δ: 7.4-7.2 (3H), 4.2 (m, 2H), 3.9 (m, 2H).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux
  3. customto crystallize
  4. customThe liquid was decanted
  5. dissolutionthe residue was dissolved in methylene chloride
  6. dry with materialdried with magnesium sulfate
  7. customThe organic residue was chromatographed on silica gel with hexanes/ethyl acetate (3:1) as eluent

Sources & evidence

ORD record
ord-405a007199384286abb5a2b4f9e210e8
Source dataset
uspto-grants-2002_03
Patent number
US06358885B1

Reaction notes

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