Naphthalenetetracarboxylic dianhydride → HCID 178457694, compound

HRID 486232Notes

Reaction equation

HRID 486232 reaction equation
[CH:1]1[C:10]2[C:11]([O:13][C:14](=[O:15])[C:8]3[C:9]=2[C:4]2[C:5]([C:16]([O:18][C:19](=[O:20])[C:3]=2[CH:2]=1)=[O:17])=[CH:6][CH:7]=3)=[O:12].[CH2:21]([NH2:24])[C:22]#[CH:23]>CN(C=O)C>[CH2:21]([N:24]=[C:14]([C:8]1[C:9]2[C:10]([C:11]([OH:13])=[O:12])=[CH:1][CH:2]=[C:3]([C:19]([OH:18])=[O:20])[C:4]=2[C:5]([C:16](=[N:24][CH2:21][C:22]#[CH:23])[OH:17])=[CH:6][CH:7]=1)[OH:15])[C:22]#[CH:23]

Participants

4

Reactant 2

HCID 6678Naphthalenetetracarboxylic dianhydrideHCID 239041Propargylamine

Product 1

HCID 178457694HCID 178457694, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
135 °C

Procedure

In a 250-ml round-bottom flask, equipped with a mechanical stirrer was placed 10.3541 g. (0.036 mole) of 1,4,5,8-naphthalene tetracarboxylic acid dianhydride in 100 ml DMF and the system purged with nitrogen. To this solution was added 4.9310 g. (0.089 mole) of propargyl amine, causing the temperature to rise to 46° C. Then heating was begun and continued at 135° C. for 5 hours. Then the apparatus was fitted with a distillation head and approximately 2 ml of distillate were removed over a one-hour period by heating at 135° C. After cooling, the solid material was isolated by filtration, washed with DMF and vacuum-dried to give a tan solid, 9.0084 g. (68.3%), recrystallization from DMAC gave 4.5840 g. of the diimide whose infrared spectrum was identical to that of Example 2(a).

Workup

  1. customIn a 250-ml round-bottom flask, equipped with a mechanical stirrer
  2. additionTo this solution was added 4.9310 g
  3. customto rise to 46° C
  4. temperatureThen heating
  5. customThen the apparatus was fitted with a distillation head and approximately 2 ml of distillate
  6. customwere removed over a one-hour period
  7. temperatureAfter cooling
  8. customthe solid material was isolated by filtration
  9. washwashed with DMF
  10. customvacuum-dried
  11. customto give a tan solid, 9.0084 g
  12. custom(68.3%), recrystallization from DMAC
  13. customgave 4.5840 g

Sources & evidence

ORD record
ord-7fdc2a0f360e4cbba55b23207981e534
Source dataset
uspto-grants-1994_03
Patent number
US05290908

Reaction notes

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