(3-Bromopropyl)benzene → HCID 467101, compound

HRID 635839Notes

Reaction equation

HRID 635839 reaction equation
[Mg].Br[CH2:3][CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[CH3:12][C:13]1[S:17][C:16]2=[N:18][CH:19]=[C:20]([CH:21]=[O:22])[N:15]2[C:14]=1[CH3:23].[Cl-].[NH4+]>CCOCC>[CH3:12][C:13]1[S:17][C:16]2=[N:18][CH:19]=[C:20]([CH:21]([CH2:3][CH2:4][CH2:5][C:6]3[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=3)[OH:22])[N:15]2[C:14]=1[CH3:23]

Participants

6

Reactant 4

HCID 12503(3-Bromopropyl)benzeneHCID 25517Ammonium ChlorideHCID 5462224MagnesiumHCID 15521025HCID 15521025, compound

Product 1

HCID 467101HCID 467101, compoundYield 31.7%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

Magnesium (0.29 g) in ether was treated with 1-bromo-3-phenylpropane (2.38 g) and reacted for 5 hours. Solid 2,3-Dimethylimidazo[2,1-b]thiazole-5-carboxaldehyde (Formula A-6) (0.72 g) was added and the viscous mixture was reacted for 1.5 hours. The thick suspension was diluted with ether and poured into cold 5% ammonium chloride solution. The mixture was extracted with ethyl acetate, the extract was dried and evaporated to a semi-crystalline residue (1.6 g). The residue, containing unreacted 2,3-Dimethylimidazo[2,1-b]thiazole-5-carboxaldehyde (Formula A-6), was triturated with ether, filtered and the filter cake (0.50 g) was recrystallized from acetonitrile to yield pure 2,3-Dimethyl-α-(3-phenylpropyl)imidazo-[2,1-b]thiazole-5-methanol (Formula A-9) (0.38 g), m.p. 167-169°.

Workup

  1. customreacted for 5 hours
  2. customthe viscous mixture was reacted for 1.5 hours
  3. extractionThe mixture was extracted with ethyl acetate
  4. customthe extract was dried
  5. customevaporated to a semi-crystalline residue (1.6 g)
  6. additionThe residue, containing unreacted 2,3-Dimethylimidazo[2,1-b]thiazole-5-carboxaldehyde (Formula A-6)
  7. customwas triturated with ether
  8. filtrationfiltered
  9. customthe filter cake (0.50 g) was recrystallized from acetonitrile

Sources & evidence

ORD record
ord-339b33a7d1b54e3aba1926bf679a070e
Source dataset
uspto-grants-2001_02
Patent number
US06191124B1

Reaction notes

Loading…