Phosphorus oxychloride → HCID 135738334, compound

HRID 1270302Notes

Reaction equation

HRID 1270302 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:13][C:12](=[O:14])[C:11]([CH:15]([NH:17][C:18](=O)[CH3:19])[CH3:16])=[N:10][N:9]=2)=[CH:4][CH:3]=1.P(Cl)(Cl)(Cl)=O>ClCCCl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:13][C:12](=[O:14])[C:11]3=[C:15]([CH3:16])[N:17]=[C:18]([CH3:19])[N:10]3[N:9]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 135553056N-{1-[3-(4-Bromophenyl)-5-oxo-4,5-dihydro-1,2,4-triazin-6-yl]ethyl}acetamide

Product 1

HCID 135738334HCID 135738334, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A solution of 10.0 g (29.66 mmol) of N-{1-[3-(4-bromophenyl)-5-oxo-4,5-dihydro-1,2,4-triazin-6-yl]ethyl} from example 7A in 340 ml of 1,2-dichloroethane is treated with 13.64 g (8.30 ml, 88.98 mmol) of phosphoryl chloride. The mixture is boiled under reflux for 15 h. After cooling, the solvent is removed. The residue is stirred with diethyl ether and filtered off with suction. The crystals are stirred for 1 h with 150 ml of saturated aqueous sodium hydrogencarbonate solution, and subsequently diluted with 100 ml of water. After 30 min, the solid is filtered off with suction, washed well with water and rewashed with petroleum ether.

Workup

  1. temperatureunder reflux for 15 h
  2. temperatureAfter cooling
  3. customthe solvent is removed
  4. filtrationfiltered off with suction
  5. stirringThe crystals are stirred for 1 h with 150 ml of saturated aqueous sodium hydrogencarbonate solution
  6. additionsubsequently diluted with 100 ml of water
  7. filtrationthe solid is filtered off with suction
  8. washwashed well with water

Sources & evidence

ORD record
ord-71b6e74f0e6b4805b45535c5d2df7c5f
Source dataset
uspto-grants-2007_04
Patent number
US07202243B2

Reaction notes

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