Hydrazine → HCID 59693403, compound

HRID 898874Notes

Reaction equation

HRID 898874 reaction equation
O=C1C2C(=CC=CC=2)C(=O)[N:3]1[CH:12]1[CH2:20][C:19]2[C:14](=[CH:15][CH:16]=[C:17]([S:21][C:22](=[O:26])[N:23]([CH3:25])[CH3:24])[CH:18]=2)[CH2:13]1.NN>CCO>[NH2:3][CH:12]1[CH2:20][C:19]2[C:14](=[CH:15][CH:16]=[C:17]([S:21][C:22](=[O:26])[N:23]([CH3:24])[CH3:25])[CH:18]=2)[CH2:13]1

Participants

4

Reactant 2

HCID 9321HydrazineHCID 86594051HCID 86594051, compound

Product 1

HCID 59693403HCID 59693403, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A 3-neck flask, equipped with a reflux condensor and mechanical stirrer, is charged with EtOH (98 mL) and dimethylthiocarbamic acid S-[2-(1,3-dioxo-1,3-dihydroisoindol-2-yl)indan-5-yl] ester (6.9 g; 20.6 mmol). Hydrazine (5.8 mL; 186 mmol) is added in 1-portion at RT and the reaction was refluxed with mechanical stirring for 30 min. The reaction is cooled to RT and the gelatinous, white solid is filtered and washed with ether several times. The ether washes are combined, evaporated under reduced pressure and the crude residue was further triturated with ether, filtered and the ether evaporated under reduced pressure to afford 4.6 g (95%) of dimethylthiocarbamic acid S-[2-aminoindan-5-yl) ester as a brown oil.

Workup

  1. customA 3-neck flask, equipped with a reflux condensor and mechanical stirrer
  2. temperaturethe reaction was refluxed
  3. filtrationthe gelatinous, white solid is filtered
  4. washwashed with ether several times
  5. customevaporated under reduced pressure
  6. customthe crude residue was further triturated with ether
  7. filtrationfiltered
  8. customthe ether evaporated under reduced pressure

Sources & evidence

ORD record
ord-41eff041d4354330bbb383154fc78802
Source dataset
uspto-grants-2008_04
Patent number
US07351857B2

Reaction notes

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