Chlorosuccinimide → HCID 68390886, compound

HRID 1522763Notes

Reaction equation

HRID 1522763 reaction equation
C1C(=O)N(Cl)C(=O)C1.[F:9][C:10]1[CH:11]=[C:12]([CH:16]=[C:17]([F:19])[CH:18]=1)[CH:13]=[N:14][OH:15].[C:20]([C:22](=[CH2:28])[C:23]([O:25][CH2:26][CH3:27])=[O:24])#[N:21].C([O-])(O)=O.[Na+]>CN(C=O)C.O>[C:20]([C:22]1([C:23]([O:25][CH2:26][CH3:27])=[O:24])[O:15][N:14]=[C:13]([C:12]2[CH:11]=[C:10]([F:9])[CH:18]=[C:17]([F:19])[CH:16]=2)[CH2:28]1)#[N:21]

Participants

7

Reactant 4

HCID 31398ChlorosuccinimideHCID 81530Ethyl cyanoacrylateHCID 516892Sodium BicarbonateHCID 57352551N-[(3,5-Difluorophenyl)methylidene]hydroxylamine

Product 1

HCID 68390886HCID 68390886, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
40 °C

Procedure

NCS (850 mg, 6.37 mmol) was added to a solution of 3,5-difluorobenzaldehyde oxime (1.00 g, 6.37 mmol) in DMF (60 ml), and the mixture was stirred at 40° C. for 1 h. Heating was then switched off, and ethyl 2-cyanoacrylate (1.20 g, 9.55 mmol) and NaHCO3 (561 mg, 6.68 mmol) were added. The mixture was stirred at RT for 2 h, and water (400 ml) was then added. The mixture was extracted with MTBE (3×50 ml), and the combined organic phases were washed with dilute sulfuric acid (0.5 M, ml), dried over Na2SO4 and concentrated. Chromatography of the residue on silica gel using the mobile phase heptane/EtOAc gave 810 mg of slightly contaminated ethyl 5-cyano-3-(3,5-difluorophenyl)-4,5-dihydro-1,2-oxazole-5-carboxylate, which was used without further purification.

Workup

  1. temperatureHeating
  2. stirringThe mixture was stirred at RT for 2 h
  3. extractionThe mixture was extracted with MTBE (3×50 ml)
  4. washthe combined organic phases were washed with dilute sulfuric acid (0.5 M, ml)
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-d89084a445c44f8a89952b78e1ae8ab2
Source dataset
uspto-grants-2015_07
Patent number
US09078442B2

Reaction notes

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