Diphenyl Ether → HCID 22397178, compound

HRID 1070641Notes

Reaction equation

HRID 1070641 reaction equation
[Cl:1][C:2]1[C:7]([NH:8][CH:9]=[C:10]([C:16]([O:18]CC)=O)[C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:6][CH:5]=[C:4]([CH3:21])[N:3]=1.C1(OC2C=CC=CC=2)C=CC=CC=1>C(Cl)Cl>[Cl:1][C:2]1[N:3]=[C:4]([CH3:21])[CH:5]=[C:6]2[C:7]=1[NH:8][CH:9]=[C:10]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[C:16]2=[O:18]

Participants

4

Reactant 2

HCID 7583Diphenyl EtherHCID 22397139HCID 22397139, compound

Product 1

HCID 22397178HCID 22397178, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of diethyl 2-(((2-chloro-6-methyl-3-pyridinyl)amino)methylene)malonate (Preparation 42, 0.59 g) is added to diphenyl ether (15 mL) and the mixture is degassed by alternately bubbling in nitrogen then subjecting to high vacuum. The mixture is heated rapidly to reflux and after 30 minutes cooled to room temperature. Diphenyl ether is distilled away under high vacuum and the residue taken up in CH2Cl2 (40 mL). The solid is collected by filtration and washed with CH2Cl2 with a second crop obtained by reducing the solvent volume of CH2Cl2 filtrate and collecting more solid. The title compound is obtained as a pale green powder, 0.24 g (47%). Physical characteristics: MS (ESI+) m/z 267 (M+H).

Workup

  1. customthe mixture is degassed
  2. customby alternately bubbling in nitrogen
  3. temperatureThe mixture is heated rapidly
  4. temperatureto reflux and after 30 minutes
  5. distillationDiphenyl ether is distilled away under high vacuum
  6. filtrationThe solid is collected by filtration
  7. washwashed with CH2Cl2 with a second crop
  8. customobtained
  9. customcollecting more solid

Sources & evidence

ORD record
ord-df177cf5d4d44f2b9178132efe9fd5c1
Source dataset
uspto-grants-2005_06
Patent number
US06903097B2

Reaction notes

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