Ethyl Acetate → HCID 21256452, compound

HRID 635844Notes

Reaction equation

HRID 635844 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5](/[CH:8]=[CH:9]/[C:10]([C:12]2[N:19]3[C:15]([S:16]C=C3)=[N:14][CH:13]=2)=O)=[CH:4][CH:3]=1.[O-]S(S([O-])=O)=O.[Na+].[Na+].[C:28](=O)(O)[O-].[Na+].C([O:36][CH2:37][CH3:38])(=O)C>C1(C)C=CC=CC=1.O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][C:10]2[S:16][C:15]3=[N:14][CH:13]=[C:38]([CH:37]=[O:36])[N:19]3[C:12]=2[CH3:28])=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 24489Sodium DithioniteHCID 516892Sodium BicarbonateHCID 86756425HCID 86756425, compound

Product 1

HCID 21256452HCID 21256452, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

A solution of 2-(4-Bromophenyl)-E-ethenylimidazo[2,1-b]thiazol-5-yl methanone (Formula B-9) (1.04 g) in toluene (160 mL) was treated with a solution prepared by dissolving Na2S2O4 (14.4 g) in water (220 mL), adding sodium bicarbonate (15.6 g) and Aliquot®336 (0.41 mL). The vigorously stirred suspension was heated at 100° for 85 hours, diluted with ethyl acetate and partitioned. The extract was washed with saline solutions, dried and evaporated to a viscous residue. The residue was chromatographed on silica gel and product was eluted with 4:1 hexane:ethyl acetate to provide 2-(4-Bromophenylethyl)-3-methylimidazo[2,1-b]thiazol-5-yl methanone (Formula B-10) (0.220 g). An aliquot was crystallized from isopropanol to yield pure 2-(4-Bromophenylethyl)-3-methylimidazo[2,1-b]thiazol-5-yl methanone (Formula B-10), m.p, 113-115°.

Workup

  1. customprepared
  2. temperatureThe vigorously stirred suspension was heated at 100° for 85 hours
  3. custompartitioned
  4. washThe extract was washed with saline solutions
  5. customdried
  6. customevaporated to a viscous residue
  7. customThe residue was chromatographed on silica gel and product
  8. washwas eluted with 4:1 hexane

Sources & evidence

ORD record
ord-aee9c18402f947ac99b657d170cdd747
Source dataset
uspto-grants-2001_02
Patent number
US06191124B1

Reaction notes

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