Hydrazine hydrate (1:1) → HCID 20207296, compound

HRID 542789Notes

Reaction equation

HRID 542789 reaction equation
[OH:1][CH:2]([CH2:15][S:16][C:17]1[S:18][C:19]([CH2:22][N:23]2[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]2)=[CH:20][CH:21]=1)[CH2:3][N:4]1C(=O)C2C(=CC=CC=2)C1=O.O.NN>C(O)C>[OH:1][CH:2]([CH2:15][S:16][C:17]1[S:18][C:19]([CH2:22][N:23]2[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]2)=[CH:20][CH:21]=1)[CH2:3][NH2:4]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 20207299HCID 20207299, compound

Product 1

HCID 20207296HCID 20207296, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

8.60 g (20 mmol) of 2-[2-hydroxy-3-[5-(1-piperidylmethyl)-2-thienylthio]propyl]-1H-isoindole-1,3-dione and 3.3 ml of hydrazine hydrate (80%) are boiled in 80 of ethanol for 3 hours. The residue obtained after the mixture has been concentrated by evaporation is taken up in 50 ml of water. 8 ml of conc. hydrochloric acid are added and the mixture is filtered. The filtrate is adjusted to pH 12 with conc. sodium hydroxide solution and extracted with 3×40 ml methylene chloride. The organic phase is dehydrated with Na2SO4 and concentrated by evaporation under vacuum. 4.9 g (82% of theoretical) of the title compound are obtained in the form of a light green oil.

Workup

  1. customThe residue obtained after the mixture
  2. concentrationhas been concentrated by evaporation
  3. addition8 ml of conc. hydrochloric acid are added
  4. filtrationthe mixture is filtered
  5. extractionextracted with 3×40 ml methylene chloride
  6. concentrationconcentrated by evaporation under vacuum

Sources & evidence

ORD record
ord-902aeb052c3341bc8523ad4d28349cdf
Source dataset
uspto-grants-1987_04
Patent number
US04659721

Reaction notes

Loading…