Diethylamine → HCID 21509986, compound

HRID 1576966Notes

Reaction equation

HRID 1576966 reaction equation
[O:1]=[C:2]1[C:14]2[CH:13]=[C:12]([C:15](Cl)=[O:16])[CH:11]=[CH:10][C:9]=2[C:8]2[C:3]1=[CH:4][C:5]([C:18](Cl)=[O:19])=[CH:6][CH:7]=2.[CH2:21]([NH:23][CH2:24][CH3:25])[CH3:22]>C(Cl)(Cl)Cl>[CH2:21]([N:23]([CH2:24][CH3:25])[C:18]([C:5]1[CH:6]=[CH:7][C:8]2[C:9]3[C:14](=[CH:13][C:12]([C:15]([N:23]([CH2:24][CH3:25])[CH2:21][CH3:22])=[O:16])=[CH:11][CH:10]=3)[C:2](=[O:1])[C:3]=2[CH:4]=1)=[O:19])[CH3:22]

Participants

4

Reactant 2

HCID 8021DiethylamineHCID 214196159-Oxo-fluorene-2,7-dicarbonyl chloride

Product 1

HCID 21509986HCID 21509986, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 61.0 g (0.2 mole) of 9-oxofluorene-2,7-dicarbonyl chloride dissolved in 600 ml of chloroform(hydrocarbon stabilized and stored over molecular sieves) is added 58.4 g (0.8 mole) of diethylamine in small increments. The solution is refluxed with stirring for an additional 4 hours, cooled, washed 3 times with water, dried over anhydrous sodium sulfate, filtered, and the volatile materials removed on a steam bath under vacuum. The resulting oil so obtained is triturated with pentane to effect solidification. The residue when recrystallized three times from ethyl acetate yields N,N,N',N'-tetraethyl-9-oxofluorene-2,7-dicarboxamide, m.p. of 142°-3°C, λmaxMeOH 265, and E 1cm1% 2011.

Workup

  1. temperatureThe solution is refluxed
  2. temperaturecooled
  3. washwashed 3 times with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. customthe volatile materials removed on a steam bath under vacuum
  7. customThe resulting oil so obtained
  8. customis triturated with pentane
  9. customThe residue when recrystallized three times from ethyl acetate

Sources & evidence

ORD record
ord-262d9d72f7f640c4aa3cad9a2f15e2cf
Source dataset
uspto-grants-1976_09
Patent number
US03983124

Reaction notes

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