3-Amino-3-(4-nitrophenyl)-2-cyanoacrylonitrile → HCID 59099563, compound

HRID 227616

Reaction equation

HRID 227616 reaction equation
[NH2:1][C:2]([C:8]1[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][CH:9]=1)=[C:3]([C:6]#[N:7])[C:4]#[N:5].P([O-])(OCC)(SCC)=[S:18]>C(O)C.O>[NH2:1]/[C:2](/[C:8]1[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][CH:9]=1)=[C:3](/[C:4]#[N:5])\[C:6](=[S:18])[NH2:7]

Participants

5

Reactant 2

HCID 140279223-Amino-3-(4-nitrophenyl)-2-cyanoacrylonitrileHCID 53249491Diethyldithiophosphate

Product 1

HCID 59099563HCID 59099563, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A suspension of Example 96C (2.1 g, 9.8 mmol) and 90% diethyl dithiophosphate (1.8 mL, 10.8 mmol) in ethanol (15 mL) and water (15 mL) was heated to reflux for 24 hours, cooled to room temperature, poured into ice water (300 mL), and filtered. The filter cake was dried to provide 2.3 g (95% yield) of the desired product. MS(ESI(−)) m/e 247 (M−H)−.

Workup

  1. temperatureto reflux for 24 hours
  2. filtrationfiltered
  3. customThe filter cake was dried

Sources & evidence

ORD record
ord-631e3ab4d3404d2c9f8160fcdda6472d
Source dataset
uspto-grants-2009_07
Patent number
US07560552B2

Linked notes

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