Ethanol → HCID 10409478, compound

HRID 733114Notes

Reaction equation

HRID 733114 reaction equation
[CH2:1]([N:3]([CH2:6][CH3:7])[CH2:4][CH3:5])[CH3:2].CSC(SC)=C[C:12]([C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:23])([F:22])[F:21])[CH:15]=1)=O.[OH2:26].[NH2:27][NH2:28].[CH2:29]([OH:31])[CH3:30]>>[O:31]=[C:29]1[C:30]2[C:16](=[CH:15][CH:14]=[CH:19][CH:18]=2)[C:17]2([CH2:5][CH2:4][N:3]([C:6]3[CH:7]=[C:12]([C:14]4[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:21])([F:22])[F:23])[CH:15]=4)[NH:28][N:27]=3)[CH2:1][CH2:2]2)[O:26]1

Participants

5

Reactant 4

HCID 702EthanolHCID 8471TriethylamineHCID 24654Hydrazine hydrate (1:1)HCID 145512033,3-Bis(methylsulfanyl)-1-[3-(trifluoromethyl)phenyl]prop-2-en-1-one

Product 1

HCID 10409478HCID 10409478, compoundYield 30%

Conditions

Temperature
80 °C

Procedure

Triethylamine (0.1.0 mL, 0.72 mmol) was added to ethanol solution (5.0 mL) of 3,3-bis(methylthio)-1-(3-trifluoromethylphenyl)-2-propen-1-one (200 mg, 0.68 mmol) and 3-oxospiro[isobenzofuran-1(3H),4′-piperidine]monohydrate hydrochloride (177 mg, 0.69 mmol), and the mixture was stirred at 80° C. for 24 hours under a nitrogen atmosphere. After that, hydrazine monohydrate (0.083 mL, 1.7 mmol) was added thereto, the mixture was stirred at 80° C. for 6 hours. The reaction mixture was concentrated, and water was added thereto, followed by extraction with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was separated and purified by a silica gel column chromatography (Biotage, Si+12M, hexane:ethyl acetate=1:1) to obtain the title compound (86 mg, 30%).

Workup

  1. stirringthe mixture was stirred at 80° C. for 6 hours
  2. concentrationThe reaction mixture was concentrated
  3. additionwater was added
  4. extractionfollowed by extraction with ethyl acetate
  5. washThe organic layer was washed with saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated in vacuo
  8. customThe residue was separated
  9. custompurified by a silica gel column chromatography (Biotage, Si+12M, hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-e5b7256963b74521a72b3da093f720e0
Source dataset
uspto-grants-2009_09
Patent number
US07589096B2

Reaction notes

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