2-Oxopropiononitrile → HCID 90195654, compound

HRID 404929Notes

Reaction equation

HRID 404929 reaction equation
[CH:1]([O:4][C:5]1[CH:22]=[CH:21][C:8]([O:9][C:10]2[S:11][C:12]([C:15]3OC(=O)[S:17][N:16]=3)=[CH:13][N:14]=2)=[CH:7][CH:6]=1)([CH3:3])[CH3:2].[C:23](#[N:27])[C:24]([CH3:26])=[O:25]>C1(C)C(C)=CC=CC=1>[CH:1]([O:4][C:5]1[CH:22]=[CH:21][C:8]([O:9][C:10]2[S:11][C:12]([C:15]3[N:27]=[C:23]([C:24](=[O:25])[CH3:26])[S:17][N:16]=3)=[CH:13][N:14]=2)=[CH:7][CH:6]=1)([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 694302-OxopropiononitrileHCID 69438128HCID 69438128, compound

Product 1

HCID 90195654HCID 90195654, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A mixture of Example 100B (2.0 g, 0.0057 mol) and excess pyruvonitrile (2 mL) in xylene was heated at reflux in a pressure tube overnight. The solvent was removed and the residue was purified on silica gel (5˜30% ethyl acetate in hexane) to give 1.74 g of product as a light yellow solid (84% yield). 1H NMR (300 MHz, CDCl3) δ ppm 1.36 (d, J=6.25 Hz, 6H) 2.77 (s, 3H) 4.46-4.61 (m, 1H) 6.89-6.99 (m, 2H) 7.18-7.25 (m, 2H) 8.03 (s, 1H). MS (ESI), M/Z: 394.0 (M+33)+.

Workup

  1. temperatureat reflux in a pressure tube overnight
  2. customThe solvent was removed
  3. customthe residue was purified on silica gel (5˜30% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-39d2c3fd370d4d8c8e172fe31eb06801
Source dataset
uspto-grants-2014_06
Patent number
US08748627B2

Reaction notes

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