Sodium hydride → HCID 57878591, compound

HRID 1672733Notes

Reaction equation

HRID 1672733 reaction equation
Cl[CH2:2][CH2:3][CH2:4][C:5]([NH:7][CH:8]1[CH2:13][CH2:12][C:11]([F:15])([F:14])[CH2:10][CH2:9]1)=[O:6].[H-].[Na+]>C1COCC1.CCOCC>[F:14][C:11]1([F:15])[CH2:12][CH2:13][CH:8]([N:7]2[CH2:2][CH2:3][CH2:4][C:5]2=[O:6])[CH2:9][CH2:10]1

Participants

5

Reactant 2

HCID 24758Sodium hydrideHCID 578785924-chloro-N-(4,4-difluoro-cyclohexyl)-butyramide

Product 1

HCID 57878591HCID 57878591, compoundYield 55%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

Heat the mixture of 4-chloro-N-(4,4-difluoro-cyclohexyl)-butyramide (0.41 g, 1.7 mmol) and 0.69 g of NaH in 17 mL of THF to 70° C. for overnight. Dilute the reaction mixture with Et2O. Filter the precipitate through a pad of celite. Wash the organic layer with saturated aqueous NaCl, dry over Na2SO4, filter and concentrate. Purify the crude material by chromatography to afford 0.19 g of the title compound: mass spectrum (m/z): 204 (M+1).

Workup

  1. temperatureHeat
  2. filtrationFilter the precipitate through a pad of celite
  3. washWash the organic layer with saturated aqueous NaCl
  4. dry with materialdry over Na2SO4
  5. filtrationfilter
  6. concentrationconcentrate
  7. customPurify the crude material by chromatography

Sources & evidence

ORD record
ord-13f9f43141344101b2d011c323a997b5
Source dataset
uspto-grants-2011_08
Patent number
US07998999B2

Reaction notes

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