9-Methoxyacridine → HCID 178419977, compound

HRID 463686Notes

Reaction equation

HRID 463686 reaction equation
CO[C:3]1[C:4]2[C:9]([N:10]=[C:11]3[C:16]=1[CH:15]=[CH:14][CH:13]=[CH:12]3)=[CH:8][CH:7]=[CH:6][CH:5]=2.Br.[NH:18]([C:20]1[S:21][CH2:22][CH2:23][N:24]=1)[NH2:19]>C(O)C>[S:21]1[CH2:22][CH2:23][NH:24][C:20]1=[N:18][N:19]=[C:3]1[C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][C:9]=2[NH:10][C:11]2[C:16]1=[CH:15][CH:14]=[CH:13][CH:12]=2

Participants

4

Reactant 2

HCID 993839-MethoxyacridineHCID 27743032-Thiazolidinone, hydrazone, hydrobromide

Product 1

HCID 178419977HCID 178419977, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

2.09 g of 9-methoxyacridine are dissolved in 50 ml of dry ethanol, treated with a solution of 1.98 g of 2-hydrazino-2-thiazoline hydrobromide in 50 ml of dry ethanol, heated to boiling under reflux for 1 hour and the solvent is removed in vacuo. The residue is treated with aqueous ammonia (1:5) and extracted with ethyl acetate. After drying the extract over sodium sulfate and evaporation, the material obtained is crystallized by the addition of pentane. There is obtained 9-acridanone (2-thiazolidinylidene)hydrazone of melting point 214°-215° (decomposition).

Workup

  1. temperatureheated
  2. temperatureunder reflux for 1 hour
  3. customthe solvent is removed in vacuo
  4. additionThe residue is treated with aqueous ammonia (1:5)
  5. extractionextracted with ethyl acetate
  6. customAfter drying the
  7. extractionextract over sodium sulfate and evaporation
  8. customthe material obtained
  9. customis crystallized by the addition of pentane

Sources & evidence

ORD record
ord-9a42fb80520f46c7866f1da388e48008
Source dataset
uspto-grants-1985_10
Patent number
US04544659

Reaction notes

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