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Water → HCID 67145878, compound

HRID 2422205
Notes
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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
ParticipantsProcedureWorkupSources & evidenceReaction notes

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;hexahydrateCatalyst
HCID 702
Ethanol
Solvent

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
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07960369B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes