Acetic Acid → HCID 86646771, compound

HRID 1890779Notes

Reaction equation

HRID 1890779 reaction equation
[O-:1][CH2:2][CH3:3].[Na+].[Na].[CH3:6][C:7]([O:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)([CH3:10])[C:8]#[N:9].C(O)(=O)C.[NH2:22][C:23]#N>C(O)C>[C:23]([N:9]=[C:8]([O:1][CH2:2][CH3:3])[C:7]([CH3:6])([O:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH3:10])#[N:22]

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 9864CyanamideHCID 2723922Sodium ethoxideHCID 5360545SodiumHCID 57467435HCID 57467435, compound

Product 1

HCID 86646771HCID 86646771, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a solution of sodium ethoxide in ethanol, freshly prepared from sodium (0.02 mol) and ethanol (50 mL), was added 2-methyl-2-phenoxypropanenitrile from Step D (0.05 mol). The mixture was stirred overnight at room temperature, and then acetic acid (0.07 mol) was added, followed by addition of NH2CN (0.05 mol). The mixture was stirred for 3 hours and the solvent was removed. The residue was purified by column chromatography on silica gel (mobile phase: petroleum ether/ethyl acetate=4:1˜1:1) to give the titled compound. 1H NMR (400 MHz, CDCl3) δ ppm 7.27 (t, J=8.0 Hz 2H), 7.05 (t, J=7.2 Hz 1H), 6.88˜6.90 (m, 2H), 4.38 (q, J=7.2 Hz, 2H), 1.61 (s, 6H), 1.39 (t, J=7.2 Hz, 3H); LCMS (ESI+) m/z 233 (M+H)+.

Workup

  1. stirringThe mixture was stirred for 3 hours
  2. customthe solvent was removed
  3. customThe residue was purified by column chromatography on silica gel (mobile phase: petroleum ether/ethyl acetate=4:1˜1:1)

Sources & evidence

ORD record
ord-bc503395b0dd4edc9d94b1d7adf9916d
Source dataset
uspto-grants-2013_08
Patent number
US08507493B2

Reaction notes

Loading…