Acetic Acid → HCID 19427054, compound

HRID 741774Notes

Reaction equation

HRID 741774 reaction equation
[CH2:1]([C:3]1[CH:4]=[C:5]([CH:7]=[CH:8][CH:9]=1)[NH2:6])[CH3:2].C(O[CH2:19][CH3:20])(OCC)(OCC)C.[C:21](O)(=O)[CH3:22]>>[CH2:1]([C:3]1[CH:4]=[C:5]([NH:6][C:5](=[N:6][C:21]2[CH:22]=[CH:9][CH:3]=[C:1]([CH2:19][CH3:20])[CH:2]=2)[CH3:4])[CH:7]=[CH:8][CH:9]=1)[CH3:2]

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 114753-EthylanilineHCID 66221Triethyl orthoacetate

Product 1

HCID 19427054HCID 19427054, compoundYield 875.9%

Procedure

A mixture of 3-ethylaniline (1.0 g, 8.25 mmol), triethyl orthoacetate (0.670 g, 4.13 mmol) and glacial acetic acid (0.019 ml, 0.33 mmol) was heated to reflux in an oil bath at 125°-140° C. for 3 hr. It was purified by flash chromatography on silica gel and the product was then crystallized from pet-ether-dichloromethane to give the title compound (0.770 g, 72%) as an off-white soft crystal. Mp 86°-87° C.

Workup

  1. temperaturewas heated
  2. temperatureto reflux in an oil bath at 125°-140° C. for 3 hr
  3. customIt was purified by flash chromatography on silica gel
  4. customthe product was then crystallized from pet-ether-dichloromethane

Sources & evidence

ORD record
ord-174dc9745ef24e4894dfd22a195ada8f
Source dataset
uspto-grants-1996_09
Patent number
US05552443

Reaction notes

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