Phosphorus oxychloride → HCID 22713467, compound

HRID 351850Notes

Reaction equation

HRID 351850 reaction equation
[Cl:1][C:2]1[CH:30]=[CH:29][C:5]2[N:6]3[C:10]([CH2:11][N:12]([CH2:15][C:16]4[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][C:17]=4[O:24][CH3:25])[C:13](=[O:14])[C:4]=2[CH:3]=1)=[C:9]([C:26]([NH2:28])=O)[N:8]=[CH:7]3.P(Cl)(Cl)(Cl)=O>O1CCOCC1>[Cl:1][C:2]1[CH:30]=[CH:29][C:5]2[N:6]3[C:10]([CH2:11][N:12]([CH2:15][C:16]4[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][C:17]=4[O:24][CH3:25])[C:13](=[O:14])[C:4]=2[CH:3]=1)=[C:9]([C:26]#[N:28])[N:8]=[CH:7]3

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 69922642HCID 69922642, compound

Product 1

HCID 22713467HCID 22713467, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

8-Chloro-5-(2,4-dimethoxy-benzyl)-6-oxo-5,6-dihydro-4H-2,5,10b-triaza-benzo[e]azulene-3-carboxylic acid amide (5.9 g, 13.8 mmol) and phosphorous oxychloride (1.4 mL, 15.2 mmol) were mixed in dioxane (55 mL) and refluxed overnight. The resulting yellow solution was evaporated and the residue purified by chromatography on silica gel in CH2Cl2/acetone 20:1. One obtained a white foam (3.5 g, 61%). m/z 408 (MH+)

Workup

  1. temperaturerefluxed overnight
  2. customThe resulting yellow solution was evaporated
  3. customthe residue purified by chromatography on silica gel in CH2Cl2/acetone 20:1

Sources & evidence

ORD record
ord-d38e712c64344873bf4d263d2fa3e370
Source dataset
uspto-grants-2004_06
Patent number
US06743789B2

Reaction notes

Loading…