Cyclobutanone → HCID 67375006, compound

HRID 515797Notes

Reaction equation

HRID 515797 reaction equation
[F:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:5]([F:9])[C:3]=1[NH2:4].[Si]([C:14]#[N:15])(C)(C)C.[C:16]1(=O)[CH2:19][CH2:18][CH2:17]1>O>[F:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:5]([F:9])[C:3]=1[NH:4][C:16]1([C:14]#[N:15])[CH2:19][CH2:18][CH2:17]1

Participants

5

Reactant 3

HCID 14496CyclobutanoneHCID 796472,6-DifluoroanilineHCID 82115Trimethylsilyl cyanide

Product 1

HCID 67375006HCID 67375006, compoundYield 86.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 2,6-difluoroaniline (0.5 g, 3.9 mmol), TMSCN (0.72 mL, 5.8 mmol), and cyclobutanone (0.43 mL, 5.8 mmol) was heated to 90° C. overnight. The mixture was poured in water and the aqueous layer was extracted with EtOAc (3×). The organics were combined, washed with brine. (2×), dried over sodium sulfate, and evaporated to dryness. The residue was purified by column chromatography on silica gel eluting with 0 to 20% EtOAc/hexanes to afford 0.7 g of 1-((2,6-difluorophenyl)amino)cyclobutanecarbonitrile as a colorless oil. 1H NMR (300 MHz, DMSO-d6) δ 7.07-7.01 (m, 2H), 6.91-6.81 (m, 1H), 6.15 (s, 1H), 2.65-2.56 (m, 2H), 2.52-2.42 (m, 2H), 2.01-1.91 (m, 2H).

Workup

  1. extractionthe aqueous layer was extracted with EtOAc (3×)
  2. washwashed with brine
  3. dry with material(2×), dried over sodium sulfate
  4. customevaporated to dryness
  5. customThe residue was purified by column chromatography on silica gel eluting with 0 to 20% EtOAc/hexanes

Sources & evidence

ORD record
ord-9ac039352efa4543912008b93ecd6e6c
Source dataset
uspto-grants-2015_08
Patent number
US09108944B2

Reaction notes

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