Hydrazine hydrate (1:1) → HCID 25137663, compound

HRID 1663115Notes

Reaction equation

HRID 1663115 reaction equation
[Cl:1][C:2]1[S:3][C:4]([CH2:7][O:8][N:9]2C(=O)C3C(=CC=CC=3)C2=O)=[CH:5][N:6]=1.O.NN>C(O)C>[Cl:1][C:2]1[S:3][C:4]([CH2:7][O:8][NH2:9])=[CH:5][N:6]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 27642802-[(2-Chloro-5-thiazolyl)methoxy]-1H-isoindole-1,3(2H)-dione

Product 1

HCID 25137663HCID 25137663, compoundYield 118.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-[(2-Chloro-1,3-thiazol-5-yl)methoxy]-1H-isoindole-1,3(2H)-dione (Bionet, 5.0 g), was suspended in ethanol (120 ml) and hydrazine monohydrate (0.83 ml) was added. The mixture was heated to reflux and stirred at this temperature for 4 hours. The mixture was cooled to room temperature and the solid material was removed by filtration. The filtrate was evaporated under reduced pressure. The residue was re-suspended in diethyl ether (400 ml) and 4M HCl in dioxane (4.25 ml) was added. The solid material was isolated by filtration and dried under vacuum, and gave the title compound (3.3 g). 13C-NMR (DMSO-d6) δ 152.5, 143.3, 133.5, 66.9.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux
  3. customthe solid material was removed by filtration
  4. customThe filtrate was evaporated under reduced pressure
  5. addition4M HCl in dioxane (4.25 ml) was added
  6. customThe solid material was isolated by filtration
  7. customdried under vacuum

Sources & evidence

ORD record
ord-68473a98e161437b89a01c5ace0a598e
Source dataset
uspto-grants-2011_10
Patent number
US08034811B2

Reaction notes

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