Hydrazine hydrate (1:1) → (4,5-Dichlorothiophen-2-yl)methanamine

HRID 844010Notes

Reaction equation

HRID 844010 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:8][N:9]2C(=O)C3C(=CC=CC=3)C2=O)[S:5][C:6]=1[Cl:7].O.NN>CO.O1CCCC1>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:8][NH2:9])[S:5][C:6]=1[Cl:7]

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 226120382-(4,5-Dichloro-thiophen-2-ylmethyl)-isoindole-1,3-dione

Product 1

HCID 22612362(4,5-Dichlorothiophen-2-yl)methanamineYield 75.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred suspension of 2-(4,5-Dichloro-thiophen-2-ylmethyl)-isoindole-1,3-dione (0.770 grams, 2.47 mmole) in methanol (30 ml) and tetrahydrofuran (10 ml) at room temperature was added hydrazine hydrate (0.395 grams, 12.3 mmole) and stirred at room temperature over night. A precipitate formed, and the mixture was concentrated to about 15 ml and filtered. The filtrate was poured into 100 ml water and extracted with diethyl ether. The combined extracts were washed with water and brine, dried over MgSO4, filtered, and concentrated to an oil which was purified via flash chromatography on silica using 5% methanol/methylene chloride as eluent to give an oil (0.341 g). MW 182.08; MS (m/e) 183 (M++1).

Workup

  1. customA precipitate formed
  2. concentrationthe mixture was concentrated to about 15 ml
  3. filtrationfiltered
  4. additionThe filtrate was poured into 100 ml water
  5. extractionextracted with diethyl ether
  6. washThe combined extracts were washed with water and brine
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated to an oil which
  10. customwas purified via flash chromatography on silica using 5% methanol/methylene chloride as eluent

Sources & evidence

ORD record
ord-d2a8beefc9fb46f6938be6db1523dca5
Source dataset
uspto-grants-2002_04
Patent number
US06380218B1

Reaction notes

Loading…