Propargyl bromide → HCID 10796999, compound

HRID 1722704Notes

Reaction equation

HRID 1722704 reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1.Br[CH2:11][C:12]#[CH:13].C(N(C(C)C)C(C)C)C.C(OCC)(=O)C>C1(C)C=CC=CC=1>[CH2:13]([NH:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1)[C:12]#[CH:11]

Participants

6

Reactant 4

HCID 7842Propargyl bromideHCID 8857Ethyl AcetateHCID 133964-AminobenzonitrileHCID 81531Diisopropylethylamine

Product 1

HCID 10796999HCID 10796999, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
90 °C

Procedure

A suspension of 23.63 g (0.2 mol) of 4-aminobenzonitrile, 32.72 g (0.22 mol) of an 80% solution of 3-bromo-1-propyne in toluene, and 38.3 ml (0.22 mol) of N-ethyl-N-(1-methylethyl)-2-propanamine in 500 ml toluene is heated at 90° C. for eighteen hours. Ethyl acetate is added to the reaction suspension, and the suspension is washed three times with water. The organic layer is separated, dried (magnesium sulfate), and concentrated to give 32.5 g of a dark brown oil which crystallizes on standing. This is dissolved in a minimum amount of toluene and applied to a column of 1 kg of flash silica gel which is packed in toluene-ethyl acetate (20:1). Elution with the same solvent gives 24.66 g (78.9%) of the product as a cream colored solid; mp 68°-70° C.

Workup

  1. washthe suspension is washed three times with water
  2. customThe organic layer is separated
  3. dry with materialdried (magnesium sulfate)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-f417cf73b6ac46d19da92a526da44a5d
Source dataset
uspto-grants-1989_08
Patent number
US04857530

Reaction notes

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