Phenethyl bromide → HCID 467114, compound

HRID 635865Notes

Reaction equation

HRID 635865 reaction equation
[Mg].Br[CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[F: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>CCOCC>[F: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 21256457HCID 21256457, compound

Product 1

HCID 467114HCID 467114, 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. The Grignard reagent was treated with solid 7-Fluoro-imidazo [2,1-b]benzothiazole-3-carboxaldehyde (Formula L-3) (0.44 g). Incomplete conversion was observed, an additional charge of Grignard reagent was added, and reacted for 24 hours. The reaction mixture was decanted into 5% ammonium chloride solution and extracted with ethyl acetate. The extract was washed, dried, and evaporated to a solid residue (0.60 g) of crude 7-Fluoro-α-(2-phenylethyl)imidazo[2,1-b]benzothiazole-3-methanol (Formula L-4). Crystallization from isopropanol solution gave pure 7-Fluoro-α-(2-phenylethyl) imidazo[2,1-b]benzothiazole-3-methanol (Formula L-4), m.p. 195-196°. Anal. Calcd for C18H15FN2OS. C, 66.24; H, 4.63; N, 8.58; S, 9.82. Found: C, 66.08; H, 4.64; N, 8.48; S, 9.72. MS m/z 326 (M+), 235, 221, 205, 193, 179, 193, 179, 166, 152, and 91. IR (mull). 3301, 1547, 1486, 1321, 1260, 1208, 1200, 1133, and 1039 cm−1. NMR (CDCl3/CD3OD) δ2.33 (q, J=7.6 Hz, 2, CH2), 2.76-3.0 (m, 2, CH2), 5.00 (t, J=7.6 Hz, 1, CH), 7.1-7.4 (m, 9, ArH, CH), 8.01 (m, 1, ArH).

Workup

  1. customreacted for 2.5 hours
  2. additionwas added
  3. customreacted for 24 hours
  4. customThe reaction mixture was decanted into 5% ammonium chloride solution
  5. extractionextracted with ethyl acetate
  6. washThe extract was washed
  7. customdried
  8. customevaporated to a solid residue (0.60 g) of crude 7-Fluoro-α-(2-phenylethyl)imidazo[2,1-b]benzothiazole-3-methanol (Formula L-4)
  9. customCrystallization from isopropanol solution

Sources & evidence

ORD record
ord-ee55813bf51e4b68b81fadad49c23990
Source dataset
uspto-grants-2001_02
Patent number
US06191124B1

Reaction notes

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