Propargyl bromide → HCID 10796999, compound

HRID 1017780Notes

Reaction equation

HRID 1017780 reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1.[CH2:10](Br)[C:11]#[CH:12].C(N(C(C)C)CC)(C)C>C1(C)C=CC=CC=1.C(OCC)(=O)C>[CH2:12]([NH:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1)[C:11]#[CH:10]

Participants

6

Reactant 3

HCID 7842Propargyl bromideHCID 133964-AminobenzonitrileHCID 81531Diisopropylethylamine

Product 1

HCID 10796999HCID 10796999, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 23.6 g (0.20 mol) of 4-amino-benzonitrile, 16.6 ml (0.22 mol) of propargyl bromide and 38.3 ml (0.22 mol) of diisopropylethylamine is heated to 90° C. in 500 ml of toluene for 27 hours. It is then diluted with ethyl acetate, washed 3× with H2O and dried over MgSO4. After removal of the solvent by distillation the crude product is purified by flash chromatography (silica gel; ethyl acetate/petroleum ether=20:80 to 75:25).

Workup

  1. washwashed 3× with H2O
  2. dry with materialdried over MgSO4
  3. customAfter removal of the solvent
  4. distillationby distillation the crude product
  5. customis purified by flash chromatography (silica gel; ethyl acetate/petroleum ether=20:80 to 75:25)

Sources & evidence

ORD record
ord-7492fb44286042a394c03c1e85d2d160
Source dataset
uspto-grants-2002_11
Patent number
US06479524B1

Reaction notes

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