1-Bromopropane → (2-Methylpent-2-yl)hydrazine hydrochloride

HRID 1534847Notes

Reaction equation

HRID 1534847 reaction equation
CC(C)=[N:3][N:4]=[C:5]([CH3:7])[CH3:6].[CH2:9]([Mg]Br)[CH2:10]C.[Mg].[CH2:15](Br)CC.[Cl-:19].[NH4+]>CCOCC>[ClH:19].[CH3:15][C:5]([NH:4][NH2:3])([CH2:6][CH2:9][CH3:10])[CH3:7]

Participants

7

Reactant 5

HCID 78401-BromopropaneHCID 25517Ammonium ChlorideHCID 79085AcetazineHCID 5462224MagnesiumHCID 178455851HCID 178455851, compound

Product 1

HCID 19908394(2-Methylpent-2-yl)hydrazine hydrochloride

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Acetone azine (93 g) is added dropwise under reflux to a solution of propylmagnesium bromide, prepared from 44.3 g of magnesium and 224 g of propyl bromide in 350 ml of ether. After heating under reflux for 3 days, the mixture is poured into an ice-cooled aqueous ammonium chloride solution (500 ml) and the product is extracted using ether. The ether phase is concentrated, and the oily residue is stirred at room temperature for 2 h in 200 ml of water and 100 ml of conc. hydrochloric acid. The non-basic components are removed using tert-butyl methyl ether and the aqueous solution is concentrated on a rotary evaporator.

Workup

  1. temperatureAfter heating
  2. temperatureunder reflux for 3 days
  3. extractionthe product is extracted
  4. concentrationThe ether phase is concentrated
  5. customThe non-basic components are removed
  6. concentrationthe aqueous solution is concentrated on a rotary evaporator

Sources & evidence

ORD record
ord-560a288de979411ab1029e56f1c28a9d
Source dataset
uspto-grants-1992_02
Patent number
US05091398

Reaction notes

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