1,2-Dibromoethane → HCID 19886439, compound

HRID 654826Notes

Reaction equation

HRID 654826 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[C:11]([C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)=[N:10][C:9](=[S:19])[N:8]=1.[H-].[Na+].Br[CH2:23][CH2:24]Br>CN(C)C=O>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[N:8]2[C:9]([S:19][CH2:23][CH2:24]2)=[N:10][C:11]=1[C:12]1[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=1.[F:18][C:15]1[CH:16]=[CH:17][C:12]([C:11]2[N:10]3[C:9]([S:19][CH2:23][CH2:24]3)=[N:8][C:7]=2[C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=2)=[CH:13][CH:14]=1

Participants

6

Reactant 3

HCID 78391,2-DibromoethaneHCID 24758Sodium hydrideHCID 19886454HCID 19886454, compound

Product 2

HCID 19886439HCID 19886439, compoundHCID 19886443HCID 19886443, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 9.76 g (0.036 mol) of 4-(2-pyridinyl)-5-(4-fluorophenyl)-imidazole-2-thione, prepared as described in part d, in 250 ml of dry N,N-dimethylformamide was treated with 3.52 g (0.073 mol) of a 50% oil dispersion of sodium hydride. The solution was stirred for 30 minutes, followed by the addition of 13.95 g (0.074 mol) of 1,2-dibromoethane. The reaction mixture was stirred for 3 hours, and then poured into ice/water. The aqueous suspension was extracted several times with methylene chloride. The combined organic layers were washed with water, dried (MgSO4), and concentrated. The products were separated by chromatography on silica gel with 10% acetonitrile in methylene chloride and 25% acetonitrile in methylene chloride as eluants. Each product was recrystallized from acetonitrile-hexane to give the title Formula (I) compounds 5-(2-pyridinyl)-6-(4-fluoro-phenyl)-2,3-dihydroimidazo[2,1-b]thiazole, m.p. 152°-154° C., and 5-(4-fluorophenyl)-6-(2-pyridinyl)-2,3-dihydroimidazo[ 2,1-b]thiazole, m.p. 164°-166° C.

Workup

  1. stirringThe reaction mixture was stirred for 3 hours
  2. extractionThe aqueous suspension was extracted several times with methylene chloride
  3. washThe combined organic layers were washed with water
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customThe products were separated by chromatography on silica gel with 10% acetonitrile in methylene chloride and 25% acetonitrile in methylene chloride as eluants
  7. customEach product was recrystallized from acetonitrile-hexane

Sources & evidence

ORD record
ord-84a8fa9e636b4e99a5c218df345344f5
Source dataset
uspto-grants-1992_07
Patent number
US05134150

Reaction notes

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