Phenethyl bromide → HCID 467108, compound

HRID 635853Notes

Reaction equation

HRID 635853 reaction equation
Br[CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[N:10]1[CH:11]=[C:12]([CH:21]=[O:22])[N:13]2[C:17]3[CH2:18][CH2:19][CH2:20][C:16]=3[S:15][C:14]=12>C1COCC1>[C:4]1([CH2:3][CH2:2][CH:21]([C:12]2[N:13]3[C:14]([S:15][C:16]4[CH2:20][CH2:19][CH2:18][C:17]=43)=[N:10][CH:11]=2)[OH:22])[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 7666Phenethyl bromideHCID 21256485HCID 21256485, compound

Product 1

HCID 467108HCID 467108, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The Grignard reagent generated during 18 hours, from (2-bromoethyl)benzene (2.2 g) an Mg (0.291 g) in THF (70 mL) was treated with solid 6,7-Dihydro-5H-cyclopent[d]imidazo[2,1-b]thiazole-3-carboxaldehyde (FIG. E-6) (0.58 g) and reacted for 1.5 hours. The supernate solution was decanted into cold 5% ammonium chloride solution and precipitated 6,7-Dihydro-α-(2-phenylethyl)-5H-cyclopent[d]imidazo[2,1-b]thiazole-3-methanol (FIG. E-7) (0.80 g) was filtered. Crystallization from acetonitrile solution gave pure 6,7-Dihydro-α-(2-phenylethyl)-5H-cyclopent[d]imidazo[2,1-b]thiazole-3-methanol (FIG. E-7), m.p. 117-118°.

Workup

  1. customreacted for 1.5 hours
  2. customThe supernate solution was decanted into cold 5% ammonium chloride solution
  3. customprecipitated 6,7-Dihydro-α-(2-phenylethyl)-5H-cyclopent[d]imidazo[2,1-b]thiazole-3-methanol (FIG. E-7) (0.80 g)
  4. filtrationwas filtered
  5. customCrystallization from acetonitrile solution

Sources & evidence

ORD record
ord-988b560da72c4d618ef29f23e9d75c0b
Source dataset
uspto-grants-2001_02
Patent number
US06191124B1

Reaction notes

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