Triphosgene → HCID 178518401, compound

HRID 1517449Notes

Reaction equation

HRID 1517449 reaction equation
[NH2:1][C:2]1[C:3]([C:15]([NH2:17])=[O:16])=[N:4][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([F:14])[CH:9]=2)=[CH:6][CH:7]=1.Cl[C:19](Cl)([O:21]C(=O)OC(Cl)(Cl)Cl)Cl>O1CCOCC1>[OH:21][C:19]1[N:17]=[C:15]([OH:16])[C:3]2[N:4]=[C:5]([C:8]3[CH:13]=[CH:12][CH:11]=[C:10]([F:14])[CH:9]=3)[CH:6]=[CH:7][C:2]=2[N:1]=1

Participants

4

Reactant 2

HCID 94429TriphosgeneHCID 576983423-Amino-6-(3-fluorophenyl)pyridine-2-carboxamide

Product 1

HCID 178518401HCID 178518401, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 3-amino-6-(3-fluorophenyl)-pyridine-2-carboxylic acid amide (0.46 g, 2.0 mmol) and triphosgene (0.30 g, 1.0 mmol) in dioxane (10 ml) was heated under reflux for 2 hours. After cooling to room temperature, the precipitate was collected by filtration and washed with diethyl ether. The title compound was obtained as a yellowish solid (410 mg, yield 80%) which was characterised as follows: MS (m/z): 258 ([M+H]+, 100).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 2 hours
  3. filtrationthe precipitate was collected by filtration
  4. washwashed with diethyl ether

Sources & evidence

ORD record
ord-22006dbf0b93472b9f4254c2feda6ece
Source dataset
uspto-grants-2012_07
Patent number
US08232278B2

Reaction notes

Loading…