Diphosgene → HCID 57864352, compound

HRID 1672688Notes

Reaction equation

HRID 1672688 reaction equation
[C:1]([C:5]1[CH:42]=[CH:41][C:8]([CH2:9][O:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2/[CH:17]=[CH:18]/[CH:19]([CH2:31][CH2:32][C:33]2[CH:38]=[CH:37][C:36]([C:39]#[N:40])=[CH:35][CH:34]=2)[CH2:20][C:21]2[CH:30]=[CH:29][C:24]([C:25]([NH:27][NH2:28])=[O:26])=[CH:23][CH:22]=2)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].Cl[C:44](OC(Cl)(Cl)Cl)=[O:45]>O1CCOCC1>[C:1]([C:5]1[CH:42]=[CH:41][C:8]([CH2:9][O:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2/[CH:17]=[CH:18]/[CH:19]([CH2:20][C:21]2[CH:30]=[CH:29][C:24]([C:25]3[O:26][C:44](=[O:45])[NH:28][N:27]=3)=[CH:23][CH:22]=2)[CH2:31][CH2:32][C:33]2[CH:38]=[CH:37][C:36]([C:39]#[N:40])=[CH:35][CH:34]=2)=[CH:7][CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 10426DiphosgeneHCID 57864419HCID 57864419, compound

Product 1

HCID 57864352HCID 57864352, compoundYield 96.6%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

A solution of 185 mg (0.29 mmol, 89% purity) of 4-{(3E)-4-{2-[(4-tert-butylbenzyl)oxy]phenyl}-2-[2-(4-cyanophenyl)ethyl]but-3-en-1-yl}benzohydrazide from Example 103A in 1 ml of dioxane is slowly added dropwise to a solution of 87.3 mg (0.44 mmol) of trichloromethyl chloroformate in 0.5 ml of dioxane. The reaction mixture is stirred under reflux for two hours. After cooling, the mixture is concentrated in vacuo, directly taken up on silica gel and purified by flash chromatography (mobile phase: dichloromethane/methanol/aq. ammonia 10:1:0.1). 166 mg (0.28 mmol, 96% yield) of an oil are isolated.

Workup

  1. temperatureunder reflux for two hours
  2. temperatureAfter cooling
  3. concentrationthe mixture is concentrated in vacuo
  4. custompurified by flash chromatography (mobile phase: dichloromethane/methanol/aq. ammonia 10:1:0.1)

Sources & evidence

ORD record
ord-6d3b56a3072540f39ef38d1046df6ff5
Source dataset
uspto-grants-2011_08
Patent number
US07998988B2

Reaction notes

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