Iodine → HCID 467112, compound

HRID 635860Notes

Reaction equation

HRID 635860 reaction equation
[Mg].Br[CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.II.[N:13]1[CH:14]=[C:15]([CH:25]=[O:26])[N:16]2[C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=3[S:18][C:17]=12>C1COCC1>[C:5]1([CH2:4][CH2:3][CH:25]([C:15]2[N:16]3[C:17]([S:18][C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=43)=[N:13][CH:14]=2)[OH:26])[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

6

Reactant 4

HCID 807Iodine2×HCID 7666Phenethyl bromide2×HCID 5462224MagnesiumHCID 21256462HCID 21256462, compound

Product 1

HCID 467112HCID 467112, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Magnesium metal (0.29 g), 12 g atom) in dry THF (70 mL) was treated with (2-bromoethyl) benzene (0.44 mL) and an Iodine crystal. When the Iodine color had discharged additional (2-bromoethyl)benzene (1.2 mL) was added and the suspension was reacted for 24 hours. Solid imidazo[2,1-b]benzothiazole-3-carboxaldehyde (Formula J-3) (0.606 g, 3.0 mmol) was added and the mixture was reacted for 1.25 hours. The solution was decanted into 5% NH4Cl solution (250 mL) and the mixture was extracted with ethyl acetate. Drying and evaporation of the extract gave pure α-(2-phenylethyl)-imidazo[2,1-b]benzothiazole-3-methanol (Formula J-4) (0.81 g) after trituration of residue with acetonitrile. An aliquot of the triturated product was crystallized from acetonitrile solution to provide an analytical sample of α-(2-phenylethyl)-imidazo[2,1-b]benzothiazole-3-methanol (Formula J-4) (m.p. 174-175°).

Workup

  1. additionwas added
  2. customthe suspension was reacted for 24 hours
  3. customthe mixture was reacted for 1.25 hours
  4. customThe solution was decanted into 5% NH4Cl solution (250 mL)
  5. extractionthe mixture was extracted with ethyl acetate
  6. customDrying
  7. customevaporation of the extract

Sources & evidence

ORD record
ord-42cdc1643b2a4ffb9516c563a41073ce
Source dataset
uspto-grants-2001_02
Patent number
US06191124B1

Reaction notes

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