Toluene → HCID 21913214, compound

HRID 1007993Notes

Reaction equation

HRID 1007993 reaction equation
[Cl:1][C:2]1[C:7]([NH2:8])=[C:6]([NH:9][CH2:10][CH2:11][O:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:5]([CH3:19])=[C:4]([CH3:20])[N:3]=1.[C:21](OCC)(OCC)(OCC)[CH3:22].C1(C)C=CC=CC=1.Cl.N1C=CC=CC=1>CO>[Cl:1][C:2]1[C:7]2[N:8]=[C:21]([CH3:22])[N:9]([CH2:10][CH2:11][O:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:6]=2[C:5]([CH3:19])=[C:4]([CH3:20])[N:3]=1

Participants

6

Reactant 4

HCID 1140TolueneHCID 66221Triethyl orthoacetateHCID 10176127Pyridinium chlorideHCID 85898826HCID 85898826, compound

Product 1

HCID 21913214HCID 21913214, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-Chloro-5,6-dimethyl-N4-(2-phenoxyethyl)pyridine-3,4-diamine (2.41 g), triethyl orthoacetate (1.60 ml), toluene (20 ml), and a catalytic amount of pyridine HCl were combined and heated to reflux for 2 hours. Methanol (15 ml) was then added and the reaction mixture was allowed to cool. The resulting white needles were filtered and dried. NMR analysis of the dried solid indicated a pure product.

Workup

  1. temperatureheated
  2. temperatureto reflux for 2 hours
  3. temperatureto cool
  4. filtrationThe resulting white needles were filtered
  5. customdried

Sources & evidence

ORD record
ord-13032641c0f84ae39e38e963deeaf890
Source dataset
uspto-grants-2004_09
Patent number
US06797718B2

Reaction notes

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