Triphosgene → HCID 86683458, compound

HRID 409556Notes

Reaction equation

HRID 409556 reaction equation
Cl[C:2](Cl)([O:4]C(=O)OC(Cl)(Cl)Cl)Cl.[NH2:13][C:14]1[CH:22]=[CH:21][C:20]([C:23]([C:25]2[N:29]3[CH:30]=[CH:31][CH:32]=[CH:33][C:28]3=[C:27]([Br:34])[N:26]=2)=[O:24])=[CH:19][C:15]=1[C:16]([OH:18])=[O:17]>O1CCOCC1>[Br:34][C:27]1[N:26]=[C:25]([C:23]([C:20]2[CH:21]=[CH:22][C:14]3[NH:13][C:2](=[O:4])[O:17][C:16](=[O:18])[C:15]=3[CH:19]=2)=[O:24])[N:29]2[CH:30]=[CH:31][CH:32]=[CH:33][C:28]=12

Participants

4

Reactant 2

HCID 94429TriphosgeneHCID 66653348HCID 66653348, compound

Product 1

HCID 86683458HCID 86683458, compoundYield 97.9%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

1.30 g (4.37 mmol) of triphosgene dissolved in 10 ml of dioxane are added, under an inert atmosphere at ambient temperature, to 1.05 g (2.91 mmol) of 2-amino-5-(1-bromoimidazo[1,5-a]pyridin-3-ylcarbonyl)benzoic acid. The reaction medium is refluxed for 4 hours, and then concentrated under reduced pressure. 100 ml of water are added to the residue. The precipitate obtained is filtered off under reduced pressure at 40° C. for 18 hours. 1.1 g of a yellow solid are obtained.

Workup

  1. temperatureThe reaction medium is refluxed for 4 hours
  2. concentrationconcentrated under reduced pressure
  3. addition100 ml of water are added to the residue
  4. customThe precipitate obtained
  5. filtrationis filtered off under reduced pressure at 40° C. for 18 hours

Sources & evidence

ORD record
ord-85d4427e801c442e8d5a8f11a1f195d5
Source dataset
uspto-grants-2014_06
Patent number
US08759344B2

Reaction notes

Loading…