Methyl Ethyl Ketone → HCID 21409920, compound

HRID 1283550Notes

Reaction equation

HRID 1283550 reaction equation
[CH3:1][NH:2][C:3]([CH3:7])([CH3:6])[C:4]#[N:5].[CH2:8](Br)[CH:9]=[CH2:10].C(=O)([O-])[O-].[Na+].[Na+].C(C(C)=O)C>CCOCC.[I-].[Na+]>[CH2:10]([CH2:1][NH:2][C:3]([CH3:7])([CH3:6])[C:4]#[N:5])[CH:9]=[CH2:8]

Participants

7

Reactant 4

HCID 6569Methyl Ethyl KetoneHCID 7841Allyl bromideHCID 10340Sodium CarbonateHCID 25302512-methyl-2-(methylamino)propanenitrile

Product 1

HCID 21409920HCID 21409920, compoundYield 48.2%

Reagents, catalysts & solvents 2

HCID 5238Sodium IodideCatalystHCID 3283Diethyl EtherSolvent2×

Procedure

A mixture of 2-methylamino-2-methylpropionitrile (14.7 g., 0.15 mole) allyl bromide (18.0 g., 0.15 mole), sodium carbonate (15.9 g., 0.15 mole), sodium iodide (0.2 g., 0.001 mole) and methyl ethyl ketone (200 ml.) was heated under reflux for 40 hrs. The sodium carbonate was filtered off and the solvent was removed from the filtrate in vacuo to give a yellow oil, T.L.C. (Silica, ether), three components RF 0.8, 0.4 and 0.0. The oil was passed through a column of silica 40 × 3.5 cm. using ether as an eluent to give 2-allylmethylamino-2-methylpropionitrile (10.0 g., 48%).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 40 hrs
  3. filtrationThe sodium carbonate was filtered off
  4. customthe solvent was removed from the filtrate in vacuo
  5. customto give a yellow oil, T.L.C

Sources & evidence

ORD record
ord-15a041ce1daf4d72a777003756a923be
Source dataset
uspto-grants-1976_08
Patent number
US03975443

Reaction notes

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