Triethyl orthoacetate → HCID 53752236, compound

HRID 2396746Notes

Reaction equation

HRID 2396746 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([N:8]([CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:5]([NH2:23])=[C:4]([NH:24][C:25]([CH3:28])([CH3:27])[CH3:26])[C:3]=1[CH3:29].[C:30](OCC)(OCC)(OCC)[CH3:31]>>[Cl:1][C:2]1[N:7]=[C:6]([N:8]([CH2:9][C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH2:16][C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:5]2[N:23]=[C:30]([CH3:31])[N:24]([C:25]([CH3:26])([CH3:28])[CH3:27])[C:4]=2[C:3]=1[CH3:29]

Participants

3

Reactant 2

HCID 66221Triethyl orthoacetateHCID 53943942HCID 53943942, compound

Product 1

HCID 53752236HCID 53752236, compound

Procedure

6-Chloro-5-methyl-N4 -(1,1-dimethylethyl)-N2,N2 -bis(phenylmethyl)pyridine-2,3,4-triamine was combined with an excess of triethyl orthoacetate and heated first on a steam bath for about 16 hours and then in an oil bath at 130° C. for 2 hours. The excess triethyl orthoacetate was distilled off under vacuum. The resulting residue was diluted with methylene chloride, washed with water and sodium bicarbonate solution, dried over magnesium sulfate then filtered through a layer of silica gel eluting with additional methylene chloride. The filtrate was concentrated under vacuum to provide a mixture which was carried on to the next step.

Workup

  1. temperatureheated first on a steam bath for about 16 hours
  2. distillationThe excess triethyl orthoacetate was distilled off under vacuum
  3. additionThe resulting residue was diluted with methylene chloride
  4. washwashed with water and sodium bicarbonate solution
  5. dry with materialdried over magnesium sulfate
  6. filtrationthen filtered through a layer of silica gel eluting with additional methylene chloride
  7. concentrationThe filtrate was concentrated under vacuum
  8. customto provide a mixture which

Sources & evidence

ORD record
ord-2ff3fc319ca644d7b1462e7fdb702c43
Source dataset
uspto-grants-1996_02
Patent number
US05494916

Reaction notes

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