Hydrazine → dimethylthiocarbamic acid S-[6-amino-5,6,7,8-tetrahydronaphthalen-2-yl) ester

HRID 898866Notes

Reaction equation

HRID 898866 reaction equation
O=C1C2C(=CC=CC=2)C(=O)[N:3]1[CH:12]1[CH2:21][CH2:20][C:19]2[CH:18]=[C:17]([S:22][C:23](=[O:27])[N:24]([CH3:26])[CH3:25])[CH:16]=[CH:15][C:14]=2[CH2:13]1.NN>CCO>[NH2:3][CH:12]1[CH2:21][CH2:20][C:19]2[CH:18]=[C:17]([S:22][C:23](=[O:27])[N:24]([CH3:25])[CH3:26])[CH:16]=[CH:15][C:14]=2[CH2:13]1

Participants

4

Reactant 2

HCID 9321HydrazineHCID 86594049dimethylthiocarbamic acid S-[6-(1,3-dioxo-1,3-dihydroisoindol-2-yl)-5,6,7,8-tetrahydronaphthalen-2-yl]ester

Product 1

HCID 86594048dimethylthiocarbamic acid S-[6-amino-5,6,7,8-tetrahydronaphthalen-2-yl) esterYield 103.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A 3-neck flask, equipped with a reflux condensor and mechanical stirrer, is charged with EtOH (115 mL) and dimethylthiocarbamic acid S-[6-(1,3-dioxo-1,3-dihydroisoindol-2-yl)-5,6,7,8-tetrahydronaphthalen-2-yl] ester (8.7 g; 23.5 mmol). Hydrazine (6.6 mL; 2.11 mol) is added in 1-portion at RT and the reaction was refluxed with mechanical stirring for 40 min. The reaction is cooled to RT and the gelatinous, white solid is filtered and washed thoroughly with ether. 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 6.1 g (100%) of dimethylthiocarbamic acid S-[6-amino-5,6,7,8-tetrahydronaphthalen-2-yl) ester as a yellow 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 thoroughly with ether
  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-db4e7fc6d7b54d0b8ab82b0656973770
Source dataset
uspto-grants-2008_04
Patent number
US07351857B2

Reaction notes

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