Phosgene → HCID 19892242, compound

HRID 893316Notes

Reaction equation

HRID 893316 reaction equation
[N+:1]([C:4]1[CH:9]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:7]=[C:6]([N+:14]([O-:16])=[O:15])[C:5]=1[NH:17][NH:18][C:19](=[O:24])[C:20]([CH3:23])([CH3:22])[CH3:21])([O-:3])=[O:2].[C:25](Cl)(Cl)=[O:26]>C1(C)C=CC=CC=1>[CH3:22][C:20]([C:19]1[O:24][C:25](=[O:26])[N:17]([C:5]2[C:4]([N+:1]([O-:3])=[O:2])=[CH:9][C:8]([C:10]([F:11])([F:12])[F:13])=[CH:7][C:6]=2[N+:14]([O-:16])=[O:15])[N:18]=1)([CH3:21])[CH3:23]

Participants

4

Reactant 2

HCID 6371Phosgene2×HCID 19892243HCID 19892243, compound

Product 1

HCID 19892242HCID 19892242, compoundYield 45.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
59 °C

Procedure

A mixture of 0.35 g (1 mmol) of N'-(2,6-dinitro-4-trifluoromethylphenyl)-2,2-dimethylpropionhydrazide, 0.3 g (3.1 mmols) of phosgene and 2.1 ml of toluene was heated to reflux for 2.5 hours (inner temperature of 59° C.). A solution (0.7 ml) of 0.1 g (1 mmol) of phosgene in toluene was further added to the reaction mixture followed by heating to reflux for further 2.5 hours. An excess of phosgene and toluene were distilled off and the residue was taken up in 20 ml of ether. After washing with saturated sodium chloride aqueous solution, the solution was dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The thus obtained crude product was subjected to silica gel column chromatography to give 0.17 g of 5-(1,1-dimethylethyl)-3-(2,6-dinitro-4-trifluoromethylphenyl)-1,3,4-oxadiazolin-2-one.

Workup

  1. temperaturewas heated
  2. temperatureby heating
  3. temperatureto reflux for further 2.5 hours
  4. distillationAn excess of phosgene and toluene were distilled off
  5. washAfter washing with saturated sodium chloride aqueous solution
  6. dry with materialthe solution was dried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe thus obtained crude product

Sources & evidence

ORD record
ord-af552e96280748a1a29f3224409edaae
Source dataset
uspto-grants-1992_06
Patent number
US05124341

Reaction notes

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