Dichloromethane → HCID 86699606, compound

HRID 1053365Notes

Reaction equation

HRID 1053365 reaction equation
O=C1C2C(=CC=CC=2)C(=O)[N:3]1[O:12][CH2:13][CH2:14][NH:15][C:16]([NH:18][C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:17].C(Cl)Cl.O.NN>C(O)C>[NH2:3][O:12][CH2:13][CH2:14][NH:15][C:16]([NH:18][C:19](=[O:25])[O:20][C:21]([CH3:23])([CH3:22])[CH3:24])=[O:17]

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-db30212a9f1540d39254c748dfbb4186
Source dataset
uspto-grants-2016_07
Patent number
US09393239B2

Reaction notes

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