1-Chloronaphthalene → HCID 22731614, compound

HRID 1608471Notes

Reaction equation

HRID 1608471 reaction equation
[C:1]1([NH2:8])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH2:7].Cl[C:10]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:13]=[CH:12][CH:11]=1>>[CH:4]1[C:3]2=[C:2]3[C:3]([C:10]4[C:19]5[C:14](=[CH:15][CH:16]=[CH:17][C:18]2=5)[CH:13]=[CH:12][CH:11]=4)=[CH:2][CH:1]=[CH:6][C:1]3=[CH:6][CH:5]=1.[N:7]1[C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][C:1]=2[NH:8][CH:10]=1.[N:7]1[C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][C:1]=2[NH:8][CH:10]=1

Participants

3

Reactant 2

HCID 70031-ChloronaphthaleneHCID 7243O-Phenylenediamine

Product 1

HCID 22731614HCID 22731614, compound

Procedure

In a 20 liter stainless steel reaction vessel were mixed 817 g (2.08 mols) of perylene-3,4,9,10-tetracarboxylic acid dianhydride, 1169 g (10.4 mols) of o-phenylenediamine, and 9.36 liters of 1-chloronaphthalene. The mixture obtained was heated to a temperature of from 240° C. to 250° C. for 3 hours with stirring and then cooled to room temperature. Then, a solid product formed was obtained by filtering the reaction mixture with a filter cloth and then washed thrice with N,N-dimethylformamide. Thereafter, the solid product was mixed with an alcohol solution of sodium hydroxide to provide a slurry. After filtering the slurry, the solid product collected was washed with N,N-dimethylformamide and then methanol, and then dried overnight in an oven at 95° C. to provide 1100 g of a bisbenzimidazole perylene pigment (a mixture of the cis form and the trans form). Furthermore, the pigment was purified by sublimation. The powder X-ray diffraction pattern of the pigment after the purification by sublimation is shown in FIG. 1 (showing strong peaks at 0.8°, 10.2°, and 12.5°).

Workup

  1. customThe mixture obtained
  2. temperaturewas heated to a temperature of from 240° C. to 250° C. for 3 hours
  3. customThen, a solid product formed
  4. customwas obtained
  5. filtrationby filtering the reaction mixture with a filter cloth
  6. washwashed thrice with N,N-dimethylformamide
  7. additionThereafter, the solid product was mixed with an alcohol solution of sodium hydroxide
  8. customto provide a slurry
  9. filtrationAfter filtering the slurry
  10. customthe solid product collected
  11. washwas washed with N,N-dimethylformamide
  12. dry with materialmethanol, and then dried overnight in an oven at 95° C.

Sources & evidence

ORD record
ord-0e77547650c648a68f5d7f16429be074
Source dataset
uspto-grants-1995_03
Patent number
US05395722

Reaction notes

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