Diphosgene → HCID 57864416, compound

HRID 1672684Notes

Reaction equation

HRID 1672684 reaction equation
Cl[C:2](OC(Cl)(Cl)Cl)=[O:3].[C:9]([C:13]1[CH:47]=[CH:46][C:16]([CH2:17][O:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2/[CH:25]=[CH:26]/[CH:27]([CH2:40][CH2:41][CH2:42][CH2:43][C:44]#[N:45])[CH2:28][CH2:29][C:30]2[CH:39]=[CH:38][C:33]([C:34]([NH:36][NH2:37])=[O:35])=[CH:32][CH:31]=2)=[CH:15][CH:14]=1)([CH3:12])([CH3:11])[CH3:10]>O1CCOCC1>[C:9]([C:13]1[CH:14]=[CH:15][C:16]([CH2:17][O:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2/[CH:25]=[CH:26]/[CH:27]([CH2:28][CH2:29][C:30]2[CH:39]=[CH:38][C:33]([C:34]3[O:35][C:2](=[O:3])[NH:37][N:36]=3)=[CH:32][CH:31]=2)[CH2:40][CH2:41][CH2:42][CH2:43][C:44]#[N:45])=[CH:46][CH:47]=1)([CH3:12])([CH3:10])[CH3:11]

Participants

4

Reactant 2

HCID 10426DiphosgeneHCID 57864411HCID 57864411, compound

Product 1

HCID 57864416HCID 57864416, compoundYield 23%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

A solution of 566.6 mg (2.86 mmol) of trichloromethyl chloroformate in 2.5 ml of dry dioxane is mixed with 1.0 g of 4-[3-((E)-2-{2-[(4-tert-butylbenzyl)oxy]phenyl}vinyl)-7-cyanoheptyl]-benzohydrazide from Example 97A (crude product) in 7.5 ml of dioxane and heated to reflux for 3 hours. The mixture is then directly taken up on silica gel, concentrated to dryness and purified by flash chromatography (mobile phase: dichloromethane/methanol 5:1). 236 mg (0.429 mmol, 23% yield based on two stages) of a solid are obtained.

Workup

  1. temperatureheated
  2. temperatureto reflux for 3 hours
  3. concentrationconcentrated to dryness
  4. custompurified by flash chromatography (mobile phase: dichloromethane/methanol 5:1)
  5. custom236 mg (0.429 mmol, 23% yield based on two stages) of a solid are obtained

Sources & evidence

ORD record
ord-1605b0eba58e4eeeb77ebc535eb9a078
Source dataset
uspto-grants-2011_08
Patent number
US07998988B2

Reaction notes

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