Ethanolamine → N-2-Hydroxyethylperylene-3,4-dicarboximide

HRID 266604Notes

Reaction equation

HRID 266604 reaction equation
[CH:1]1[C:18]2=[C:19]3[C:8]([C:9]4[C:20]5[C:13](=[CH:14][CH:15]=[CH:16][C:17]2=5)[CH:12]=[CH:11][CH:10]=4)=[CH:7][CH:6]=[C:5]2[C:21](O[C:24](=[O:25])[C:3](=[C:4]23)[CH:2]=1)=[O:22].[NH2:26][CH2:27][CH2:28][OH:29].N1C=CN=C1.C(C(N1C(=O)C2C3C4C(=CC=2)C2C5C(C=CC=2)=CC=CC=5C=4C=CC=3C1=O)CCCCCC)CCCCC>>[OH:29][CH2:28][CH2:27][N:26]1[C:24](=[O:25])[C:3]2[C:4]3[C:19]4[C:18](=[CH:1][CH:2]=2)[C:17]2[C:20]5[C:13]([CH:14]=[CH:15][CH:16]=2)=[CH:12][CH:11]=[CH:10][C:9]=5[C:8]=4[CH:7]=[CH:6][C:5]=3[C:21]1=[O:22]

Participants

5

Reactant 4

HCID 700EthanolamineHCID 795ImidazoleHCID 11443487N-(1-Hexylheptyl)perylene-3,4-dicarboximideHCID 11759069Perylene-3,4-dicarboxylic anhydride

Product 1

HCID 12287885N-2-Hydroxyethylperylene-3,4-dicarboximide

Procedure

190 mg (0.56 mmol) of perylene-3,4-dicarboxylic anhydride are reacted with 0.85 ml (1.40 mmol) of 2-aminoethanol and 1.18 g of imidazole under an argon inert atmosphere for 96 h as in 2c, and the reaction product is worked up and dried in a drying cabinet. To remove unreacted starting material, it is boiled in 10 per cent potassium carbonate solution and washed with hot water until the filtrate run-off is colourless. The brown-red product is dried in a drying cabinet at 120° C. and then recrystallized by extraction with toluene. Yield 50 mg (23%), m.p. >260° C. UV (CHCl3): λmax =489 nm, 509. Fluorescence (CHCl3, exc. 489 nm) λmax (Irel =546 nm (1), 579 (sh, 0.46).

Workup

  1. customdried in a drying cabinet
  2. customTo remove unreacted
  3. washwashed with hot water until the filtrate
  4. customThe brown-red product is dried in a drying cabinet at 120° C.
  5. customrecrystallized by extraction with toluene

Sources & evidence

ORD record
ord-76d33a3060764c92855f7411bf838700
Source dataset
uspto-grants-1997_07
Patent number
US05650513

Reaction notes

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