Toluene → HCID 618949, compound

HRID 371444Notes

Reaction equation

HRID 371444 reaction equation
[CH3:1][C:2]([N:4](C)C)=O.[C:7]1(=[O:17])[O:12][C:10](=O)[C:9]2=[CH:13][CH:14]=[CH:15][CH:16]=[C:8]12.[K+].[Br-].[C:20]1(C)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>>[C:24]([C:25]1[CH:1]=[C:2]([N:4]2[C:7](=[O:17])[C:8]3=[CH:16][CH:15]=[CH:14][CH:13]=[C:9]3[C:10]2=[O:12])[CH:22]=[CH:21][CH:20]=1)#[CH:23]

Participants

5

Reactant 4

HCID 1140TolueneHCID 6811Phthalic AnhydrideHCID 31374DimethylacetamideHCID 253877Potassium Bromide

Product 1

HCID 618949HCID 618949, compound

Procedure

To a reaction apparatus as described in Example 1 which was maintained under a positive pressure of argon was added 20 g (0.171 mole) APA and 125 ml of DMA. To this stirred solution was slowly added 25.3 g (0.171 mole) phthalic anhydride at such a rate as to maintain the temperature of the mixture below 50° C. The mixture was then stirred for 1 hour at room temperature. Seventy (70) ml of toluene was added to the flask and the mixture was heated to azeotropic distillation to remove the water of imidization. When no further water was collected the remainder of the toluene was distilled. The reaction solution (at 50° C.) was poured into 1500 ml of distilled water. The imide (V) precipitated, was filtered, washed with water, and then dried in an air circulating oven at 95° C. overnight to yield 39.5 g (0.160 mole, 93% theoretical). The imide had a melting point of 197°-198° C. (387° F.). IR (KBr) analysis: 3280 cm-1 (--C≡CH), 1780 and 1720 cm-1 (imide C=0 ).

Workup

  1. temperaturewas maintained under a positive pressure of argon
  2. temperatureto maintain the temperature of the mixture below 50° C
  3. temperaturethe mixture was heated to azeotropic distillation
  4. customto remove the water of imidization
  5. customWhen no further water was collected the remainder of the toluene
  6. distillationwas distilled
  7. additionThe reaction solution (at 50° C.) was poured into 1500 ml of distilled water
  8. customThe imide (V) precipitated
  9. filtrationwas filtered
  10. washwashed with water
  11. customdried in an air
  12. customat 95° C.
  13. customovernight
  14. customto yield 39.5 g (0.160 mole, 93% theoretical)
  15. customa melting point of 197°-198° C. (387° F.)

Sources & evidence

ORD record
ord-83b58a161e824d13845b094bf4aa4ac4
Source dataset
uspto-grants-1985_07
Patent number
US04532270

Reaction notes

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