Phenethyl bromide → HCID 467111, compound

HRID 635857Notes

Reaction equation

HRID 635857 reaction equation
[Mg].Br[CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[N:11]1[CH:12]=[C:13]([CH:25]=[O:26])[N:14]2[C:18]3[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][C:17]=3[S:16][C:15]=12>C1COCC1>[C:5]1([CH2:4][CH2:3][CH:25]([C:13]2[N:14]3[C:15]([S:16][C:17]4[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][C:18]=43)=[N:11][CH:12]=2)[OH:26])[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 7666Phenethyl bromideHCID 5462224MagnesiumHCID 21256498HCID 21256498, compound

Product 1

HCID 467111HCID 467111, compoundYield 77.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Magnesium (0.29 g) in THF (70 mL) was treated with (2-bromoethyl) benzene (2.22 g) and the Grignard reagent was generated during 24 hours. Solid 5,6,7,8,9,10-Hexahydro-cyclooct[d]imidazo[2,1-b]thiazole-3-carboxaldehyde (Formula H-6) (0.70 g) was added, reacted for 2.5 hours and the supernate was decanted into 5% ammonium chloride solution. The precipitated 5,6,7,8,9,10-Hexahydro-α-(2-phenylethyl)cyclooct[d]imidazo-[2,1-b]-thiazole-3-methanol (Formula H-7) was extracted into ethyl acetate, the extracts were washed, dried, and evaporated to a viscous residue (1.51 g). Crystallization of the residue from acetonitrile solution provided pure 5,6,7,8,9,10-Hexahydro-α-(2-phenylethyl)cyclooct[d]imidazo-[2,1-b]thiazole-3-methanol (Formula H-7) (0.79 g), m.p. 123-124°.

Workup

  1. customreacted for 2.5 hours
  2. customthe supernate was decanted into 5% ammonium chloride solution
  3. extractionThe precipitated 5,6,7,8,9,10-Hexahydro-α-(2-phenylethyl)cyclooct[d]imidazo-[2,1-b]-thiazole-3-methanol (Formula H-7) was extracted into ethyl acetate
  4. washthe extracts were washed
  5. customdried
  6. customevaporated to a viscous residue (1.51 g)
  7. customCrystallization of the residue from acetonitrile solution

Sources & evidence

ORD record
ord-827728d7a0514072a12231dee34d4255
Source dataset
uspto-grants-2001_02
Patent number
US06191124B1

Reaction notes

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