Propargyl bromide → HCID 14650031, compound

HRID 1722703Notes

Reaction equation

HRID 1722703 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH2:8])=[O:7])=[CH:4][CH:3]=1.Br[CH2:12][C:13]#[CH:14].CC1C=CC=C(C)N=1>C1(C)C=CC=CC=1.CC(N(C)C)=O>[CH2:14]([NH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH2:8])=[O:7])=[CH:4][CH:3]=1)[C:13]#[CH:12]

Participants

6

Reactant 3

HCID 7842Propargyl bromideHCID 79372,6-LutidineHCID 760794-Aminobenzamide

Product 1

HCID 14650031HCID 14650031, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 31374DimethylacetamideSolvent

Conditions

Temperature
60 °C

Procedure

A suspension of 13.62 g (0.1 mol) of 4-aminobenzamide, 17.85 g (0.12 mol) of an 80% solution of 3-bromo-1-propyne in toluene, and 13.98 ml (0.12 mol) of 2,6-dimethylpyridine in 140 ml of dimethylacetamide (DMA) is stirred at 60° C. for two hours and then at 90° C. for one hour. The solution is cooled and the precipitated solid is collected and discarded. The filtrate is poured into a water-ice mixture and stirred. The suspension is extracted with ethyl acetate. The ethyl acetate solution is separated, dried (magnesium sulfate), and concentrated to give 20.7 g of a brown liquid. This is applied to a column of 1 kg of flash silica gel packed in dichloromethane-methanol (50:1). Elution with the same solvent gives 6.73 g (38.7%) of the product as a yellow solid, mp 139°-141° C.

Workup

  1. waitat 90° C. for one hour
  2. temperatureThe solution is cooled
  3. customthe precipitated solid is collected
  4. additionThe filtrate is poured into a water-ice mixture
  5. stirringstirred
  6. extractionThe suspension is extracted with ethyl acetate
  7. customThe ethyl acetate solution is separated
  8. dry with materialdried (magnesium sulfate)
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-1e9f50567f7347c89f876db01dff5007
Source dataset
uspto-grants-1989_08
Patent number
US04857530

Reaction notes

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