1-Bromo-4-phenylbutane → HCID 467105, compound

HRID 635848Notes

Reaction equation

HRID 635848 reaction equation
[Mg].Br[CH2:3][CH2:4][CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[CH3:13][C:14]1[N:15]2[C:21]([CH:22]=[O:23])=[CH:20][N:19]=[C:16]2[S:17][CH:18]=1>CCOCC>[CH3:13][C:14]1[N:15]2[C:21]([CH:22]([CH2:3][CH2:4][CH2:5][CH2:6][C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=3)[OH:23])=[CH:20][N:19]=[C:16]2[S:17][CH:18]=1

Participants

5

Reactant 3

HCID 2596681-Bromo-4-phenylbutaneHCID 5462224MagnesiumHCID 21256490174209-00-8

Product 1

HCID 467105HCID 467105, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Magnesium (0.15 g) in ether (15 mL) was treated with 1-bromo-4-phenylbutane (prepared by the procedure described in Kamijo et al., Chem. Phar. Bull., 1983, 31, 4189) (1.50 g) at 0° and the mixture was reacted at 25° for 2.5 hours. The suspension was cooled to 0°, solid 3-Methylimidazo[2,1-b]thiazole-5-carboxaldehyde (FIG. C-6) (0.332 g) was added and the mixture was reacted at 25° for 3 hours. The solution was decanted into 5% NH4Cl solution and extracted with ethyl acetate. The extract was dried, evaporated and the residue (0.55 g) was crystallized from acetonitrile solution to yield pure 3-Methyl-α-(4-phenylbutyl)imidazo-[2,1-b]thiazole-5-methanol (FIG. C-7) (0.39 g), m.p. 120-121°.

Workup

  1. customprepared by the procedure
  2. custom, 1983, 31, 4189) (1.50 g) at 0° and the mixture was reacted at 25° for 2.5 hours
  3. temperatureThe suspension was cooled to 0°
  4. customthe mixture was reacted at 25° for 3 hours
  5. customThe solution was decanted into 5% NH4Cl solution
  6. extractionextracted with ethyl acetate
  7. customThe extract was dried
  8. customevaporated
  9. customthe residue (0.55 g) was crystallized from acetonitrile solution

Sources & evidence

ORD record
ord-4c5141791993417d902c22515a706ab2
Source dataset
uspto-grants-2001_02
Patent number
US06191124B1

Reaction notes

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