Dichloromethane → HCID 86699606, compound

HRID 2400650Notes

Reaction equation

HRID 2400650 reaction equation
[C:1]([O:5][C:6](=[O:25])[NH:7][C:8](=[O:24])[NH:9][CH2:10][CH2:11][O:12][N:13]1C(=O)C2C(=CC=CC=2)C1=O)([CH3:4])([CH3:3])[CH3:2].C(Cl)Cl.O.NN>C(O)C>[NH2:13][O:12][CH2:11][CH2:10][NH:9][C:8]([NH:7][C:6](=[O:25])[O:5][C:1]([CH3:3])([CH3:2])[CH3:4])=[O:24]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 24654Hydrazine hydrate (1:1)HCID 86699604HCID 86699604, compound

Product 1

HCID 86699606HCID 86699606, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a mixture of tert-butyl({2-[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)oxy]ethyl}carbamoyl)carbamate 83 (0.56 g, 1.59 mmol) in a solution of DCM (10 mL) and ethanol (2 mL) was added hydrazine hydrate (0.091 mL, 1.59 mmol) at room temperature. The mixture was stirred at room temperature overnight, filtered and concentrated to provide a residue which was subjected to chromatography to give 84 (0.25 g, 72%) as a white solid.

Workup

  1. filtrationfiltered
  2. concentrationconcentrated
  3. customto provide a residue which

Sources & evidence

ORD record
ord-ff9df62bf0f945589530f377a40419f4
Source dataset
uspto-grants-2014_08
Patent number
US08796257B2

Reaction notes

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