Phenethyl bromide → HCID 467115, compound

HRID 635868Notes

Reaction equation

HRID 635868 reaction equation
[Mg].Br[CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[CH3:11][O:12][C:13]1[CH:26]=[CH:25][C:16]2[N:17]3[C:22]([CH:23]=[O:24])=[CH:21][N:20]=[C:18]3[S:19][C:15]=2[CH:14]=1>CCOCC>[CH3:11][O:12][C:13]1[CH:26]=[CH:25][C:16]2[N:17]3[C:22]([CH:23]([CH2:3][CH2:4][C:5]4[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=4)[OH:24])=[CH:21][N:20]=[C:18]3[S:19][C:15]=2[CH:14]=1

Participants

5

Reactant 3

HCID 7666Phenethyl bromideHCID 5462224MagnesiumHCID 21256465HCID 21256465, compound

Product 1

HCID 467115HCID 467115, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Magnesium (0.146 g) in anhydrous ether (15 mL) was treated with (2-bromoethyl)benzene (0.82 mL) and reacted for 2.5 hours. Solid 7-Methoxy-imidazo[2,1-b]benzothiazole-3-carboxaldehyde (Formula M-3) (0.46 g) was added and reacted for 24 hours. The reaction mixture was quenched with 5% ammonium chloride solution and product was extracted into ethyl acetate. Drying and evaporation of solvent gave crude 7-Methoxy-α-(2-phenylethyl) imidazo[2,1-b]benzothiazole-3-methanol (Formula M-4) which was recrystallized from acetonitrile solution to provide pure 7-Methoxy-α-(2-phenylethyl)imidazo[2,1-b]benzothiazole-3-methanol (Formula M-4) (0.60 g), m.p. 166-167°.

Workup

  1. customreacted for 2.5 hours
  2. customreacted for 24 hours
  3. customThe reaction mixture was quenched with 5% ammonium chloride solution and product
  4. extractionwas extracted into ethyl acetate
  5. customDrying
  6. customevaporation of solvent
  7. customgave crude 7-Methoxy-α-(2-phenylethyl) imidazo[2,1-b]benzothiazole-3-methanol (Formula M-4) which
  8. customwas recrystallized from acetonitrile solution

Sources & evidence

ORD record
ord-6314b959e46b410f805c84634918ec24
Source dataset
uspto-grants-2001_02
Patent number
US06191124B1

Reaction notes

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