O-Phenylenediamine → Benzimidazole perylene

HRID 279821Notes

Reaction equation

[CH:1]1[C:10]2[C:11]3[CH:20]=[CH:19][C:18]4C(OC(=O)[C:16]5[C:17]=4[C:12]=3[C:13](=[CH:14][CH:15]=5)[C:8]3[C:9]=2[C:4]2[C:5](C(OC(=O)[C:3]=2[CH:2]=1)=O)=[CH:6][CH:7]=3)=O.[C:31]1([NH2:38])[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=1[NH2:37]>C(O)(=O)C>[CH:14]1[C:13]2=[C:12]3[C:11]([C:10]4[C:9]5[C:4](=[CH:5][CH:6]=[CH:7][C:8]2=5)[CH:3]=[CH:2][CH:1]=4)=[CH:20][CH:19]=[CH:18][C:17]3=[CH:16][CH:15]=1.[N:37]1[C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][C:31]=2[NH:38][CH:1]=1

Participants

Conditions

Temperature: 210 °C

Procedure

There was mixed in a three-liter flask 5.85 grams of 3,4,9,10-perylenetetracarboxylic dianhydride, 26.77 grams of o-phenylene diamine and 7 milliliters of glacial acetic acid. The mixture resulting was then heated with stirring for 8 hours at 210° C., followed by cooling to room temperature. A solid product was then obtained by filtering the mixture throught a sintered glass funnel; followed by washing with 1,000 milliliters of methanol. Thereafter, the solid was slurried with 500 milliliters of 1 percent sodium hydroxide solution. After filtration, the solid was washed with 600 milliliters of water, and then was dried in an oven at 80° C. overnight yielding 7.62 grams, of the above product III.

Workup

customThe mixture resulting
temperaturewas then heated
temperatureby cooling to room temperature
customA solid product was then obtained
filtrationby filtering the mixture
washby washing with 1,000 milliliters of methanol
filtrationAfter filtration
washthe solid was washed with 600 milliliters of water
customwas dried in an oven at 80° C. overnight
customyielding 7.62 grams

Sources & evidence

ORD record: ord-5e4f46d69c54467d9e070f6592ac4651
Source dataset: uspto-grants-1986_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04587189

Reaction notes

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