Water → HCID 67145878, compound

HRID 2422205Notes

Reaction equation

HRID 2422205 reaction equation
[CH3:1][N:2]([CH2:14][C:15]1[CH:20]=[CH:19][C:18](/[CH:21]=[CH:22]/[C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:17][CH:16]=1)[C:3]1[S:4][CH:5]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:7]=1.[BH4-].[Na+].O>C(O)C.O.O.O.O.O.O.[Ni](Cl)Cl>[CH3:1][N:2]([CH2:14][C:15]1[CH:16]=[CH:17][C:18]([CH2:21][CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:19][CH:20]=1)[C:3]1[S:4][CH:5]=[C:6]([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:7]=1

Participants

6

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 67146901HCID 67146901, compound

Product 1

HCID 67145878HCID 67145878, compoundYield 64.1%

Reagents, catalysts & solvents 2

HCID 11791229Dichloronickel;hexahydrateCatalystHCID 702EthanolSolvent

Procedure

To a solution of ethyl (E)-3-[4-[[methyl(4-phenyl-2-thiazolyl)amino]methyl]phenyl]propenoate (0.60 g, 1.6 mmol) and nickel chloride hexahydrate (0.41 g, 3.2 mmol) in ethanol (25 mL) was added sodium borohydride (0.30 g, 8.0 mmol), and the mixture was stirred at room temperature for 2 hrs. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with water, dried and concentrated. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=18:1) to give the title compound (0.39 g, yield 64%). oil.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with water
  3. customdried
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=18:1)

Sources & evidence

ORD record
ord-6c718d2071a34d3991af141eef4e5cec
Source dataset
uspto-grants-2011_06
Patent number
US07960369B2

Reaction notes

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