Propargyl bromide → HCID 11286598, compound

HRID 891965Notes

Reaction equation

HRID 891965 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[C:5]#[N:6].[CH2:10](Br)[C:11]#[CH:12].C(N(C(C)C)C(C)C)C>C1(C)C=CC=CC=1.C(OCC)(=O)C>[CH2:12]([NH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[C:5]#[N:6])[C:11]#[CH:10]

Participants

6

Reactant 3

HCID 7842Propargyl bromideHCID 167023-AminobenzonitrileHCID 81531Diisopropylethylamine

Product 1

HCID 11286598HCID 11286598, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

11.8 g (0.1 mol) of 3-aminobenzonitrile and 12.3 ml (0.11 mol) of propargyl bromide (80% in toluene) are stirred in 250 ml toluene and 19.2 ml (0.11 mol) of N-ethyl-diisopropylamine for 18 hours at 90° C. After cooling the mixture is diluted with ethyl acetate and washed with water. The combined organic extracts are dried and concentrated by evaporation. The residue is chromatographed on silica gel, eluting with dichloromethane/ethanol in the ratio 98:2.

Workup

  1. temperatureAfter cooling the mixture
  2. washwashed with water
  3. customThe combined organic extracts are dried
  4. concentrationconcentrated by evaporation
  5. customThe residue is chromatographed on silica gel
  6. washeluting with dichloromethane/ethanol in the ratio 98:2

Sources & evidence

ORD record
ord-33c08d9772574b378d16ac39ab86f5fe
Source dataset
uspto-grants-2006_02
Patent number
US07005437B2

Reaction notes

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