Cyclobutanone → HCID 67132096, compound

HRID 245003Notes

Reaction equation

HRID 245003 reaction equation
C[Si]([C:5]#[N:6])(C)C.Cl.[CH3:8][S:9]([C:12]1[CH:17]=[CH:16][C:15]([NH2:18])=[CH:14][CH:13]=1)(=[O:11])=[O:10].[C:19]1(=O)[CH2:22][CH2:21][CH2:20]1.S([O-])([O-])(=O)=O.[Na+].[Na+]>CN(C=O)C>[CH3:8][S:9]([C:12]1[CH:17]=[CH:16][C:15]([NH:18][C:19]2([C:5]#[N:6])[CH2:22][CH2:21][CH2:20]2)=[CH:14][CH:13]=1)(=[O:10])=[O:11]

Participants

6

Reactant 4

HCID 14496CyclobutanoneHCID 24436Sodium SulfateHCID 82115Trimethylsilyl cyanideHCID 27351804-(Methylsulfonyl)aniline hydrochloride

Product 1

HCID 67132096HCID 67132096, compoundYield 22%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

Trimethylsilyl cyanide (0.4 g, 4 mmol) was added dropwise to a mixture of 4-methanesulfonylphenylamine hydrochloride (0.415 g, 2 mmol), cyclobutanone (0.28 g, 4 mmol) and sodium sulfate (1 g) in DMF (3 ml). The mixture was stirred for 15 hours at 120° C. After filtration to remove the sodium sulfate, the filtrate was washed with brine and extracted with ethyl acetate. The organic layer was concentrated and chromatographed (dichloromethane:acetone, 90:10) to yield 1-(4-methanesulfonylphenylamino)cyclobutanecarbonitrile (45a) (0.116 g, 0.44 mmol, 22%) as a yellowish solid. 4-methanesulfonylphenylamine (0.201 g, 1.17 mmol, 59%) was also recovered.

Workup

  1. filtrationAfter filtration
  2. customto remove the sodium sulfate
  3. washthe filtrate was washed with brine
  4. extractionextracted with ethyl acetate
  5. concentrationThe organic layer was concentrated
  6. customchromatographed (dichloromethane:acetone, 90:10)

Sources & evidence

ORD record
ord-d717b19d595a415b9f7fe2547f614abf
Source dataset
uspto-grants-2014_02
Patent number
US08658681B2

Reaction notes

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