HCID 14855720, compound → HCID 14855719, compound

HRID 1769227Notes

Reaction equation

HRID 1769227 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][CH:13]=[C:12]2[C:18]1[C:19]([NH:21][C:22](=[O:33])[C:23]=1[C:24]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[NH:26][CH:25]=1)=[O:20])C1C=CC=CC=1.Cl.[NH+]1C=CC=CC=1>C1(C)C=CC=CC=1.C(O)C>[OH:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][CH:13]=[C:12]2[C:18]1[C:19]([NH:21][C:22](=[O:33])[C:23]=1[C:24]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[NH:26][CH:25]=1)=[O:20]

Participants

4

Reactant 2

HCID 14855720HCID 14855720, compoundHCID 21584435Pyridinium hydrochloride

Product 1

HCID 14855719HCID 14855719, compound

Reagents, catalysts & solvents 1

HCID 21863594Toluene ethanolSolvent

Procedure

0.15 g (0.34 mmol) 2-(5-benzyloxy-1H-indol-3-yl)-3-(1H-indol-3-yl)-maleinimide and 4.0 g (34 mmol) pyridinium hydrochloride are heated under an atmosphere of nitrogen for 1 hour at 150° C. After cooling, the reaction mixture is diluted with ice water and extracted with ethyl acetate. The organic phase is washed out with water and evaporated to dryness. The solid residue is triturated with a little water, filtered off with suction and dried in a vacuum at 0.1 Torr and 80° C. There are obtained 85 mg (73% of theory) of dark red product; m.p. 200°-205° C.; RF=0.29 (toluene/ethanol 10:2 v/v).

Workup

  1. temperatureAfter cooling
  2. extractionextracted with ethyl acetate
  3. washThe organic phase is washed out with water
  4. customevaporated to dryness
  5. customThe solid residue is triturated with a little water
  6. filtrationfiltered off with suction
  7. customdried in a vacuum at 0.1 Torr and 80° C
  8. customThere are obtained 85 mg (73% of theory) of dark red product

Sources & evidence

ORD record
ord-9245bec7ff8e4e7eae06fa4b4f6cf0f6
Source dataset
uspto-grants-1995_01
Patent number
US05380746

Reaction notes

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