Phenethyl bromide → HCID 467113, compound

HRID 635862Notes

Reaction equation

HRID 635862 reaction equation
[Mg].Br[CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[CH3:11][C:12]1[CH:25]=[CH:24][C:15]2[N:16]3[C:21]([CH:22]=[O:23])=[CH:20][N:19]=[C:17]3[S:18][C:14]=2[CH:13]=1>C1COCC1>[CH3:11][C:12]1[CH:25]=[CH:24][C:15]2[N:16]3[C:21]([CH:22]([CH2:3][CH2:4][C:5]4[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=4)[OH:23])=[CH:20][N:19]=[C:17]3[S:18][C:14]=2[CH:13]=1

Participants

5

Reactant 3

HCID 7666Phenethyl bromideHCID 5462224MagnesiumHCID 21256443HCID 21256443, compound

Product 1

HCID 467113HCID 467113, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Magnesium (0.29 g, 12 g atom) in THF (60 mL) was treated with (2-bromoethyl)-benzene (1.64 mL) and reacted for 18 hours. The suspension was treated with solid 7-Methyl-imidazo [2,1-b]benzothiazole-3-carboxaldehyde (Formula K-3) (0.65 g) and reacted for 2 hours. The reaction mixture was decanted into cold 5% ammonium chloride solution and precipitated 7-Methyl-α-(2-phenylethyl)imidazo[2,1-b]benzothiazole-3-methanol (Formula K-4) (0.96 g) was filtered. An aliquot was crystallized from methylene chloride/ethanol solution to yield pure 7-Methyl-α-(2-phenylethyl) imidazo[2,1-b]benzothiazole-3-methanol (Formula K-4), m.p. 209-210°.

Workup

  1. customreacted for 18 hours
  2. customreacted for 2 hours
  3. customThe reaction mixture was decanted into cold 5% ammonium chloride solution
  4. customprecipitated 7-Methyl-α-(2-phenylethyl)imidazo[2,1-b]benzothiazole-3-methanol (Formula K-4) (0.96 g)
  5. filtrationwas filtered
  6. customAn aliquot was crystallized from methylene chloride/ethanol solution

Sources & evidence

ORD record
ord-9162eebb60d14e58a6db35c7cfa71cba
Source dataset
uspto-grants-2001_02
Patent number
US06191124B1

Reaction notes

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