HCID 136346398, compound → HCID 59496766, compound

HRID 449495Notes

Reaction equation

HRID 449495 reaction equation
[C:1]1([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:6]=[CH:5][C:4]([CH2:7][C:8]([C:11]2[S:12][CH:13]=[CH:14][N:15]=2)=[N:9]O)=[CH:3][CH:2]=1>C(O)(=O)C.[Zn]>[C:1]1([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:2]=[CH:3][C:4]([CH2:7][CH:8]([C:11]2[S:12][CH:13]=[CH:14][N:15]=2)[NH2:9])=[CH:5][CH:6]=1

Participants

4

Reactant 1

HCID 136346398HCID 136346398, compound

Product 1

HCID 59496766HCID 59496766, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

Zinc (60 mg, 0.9 mmol) was added to a solution of a mixture of 2-biphenyl-4-yl-1-(1,3-thiazol-2-yl)ethanone oxime (60 mg) in acetic acid (1 mL). The reaction was stirred for 3 h., was filtered and concentrated under reduced pressure. The crude was made basic with saturated NaHCO3, and was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over magnesium sulfate, filtered and concentrated under reduced pressure to give 2-biphenyl-4-yl-1-(1,3-thiazol-2-yl)ethanamine (40 mg, 80%) as a white solid. Analytical LCMS (M+H)+: m/z=280.9.

Workup

  1. filtrationwas filtered
  2. concentrationconcentrated under reduced pressure
  3. extractionwas extracted with ethyl acetate
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-54fa6a892aa64a57af115516d08fb6ca
Source dataset
uspto-grants-2013_07
Patent number
US08481732B2

Reaction notes

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