Bromoacetonitrile → HCID 86613167, compound

HRID 746765Notes

Reaction equation

HRID 746765 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([Br:10])=[C:6]([CH:9]=1)[C:7]#[N:8].[CH:11]([N:14](CC)C(C)C)(C)[CH3:12].BrCC#N>C1COCC1>[Br:10][C:5]1[CH:4]=[CH:3][C:2]([NH:1][CH2:12][C:11]#[N:14])=[CH:9][C:6]=1[C:7]#[N:8]

Participants

5

Reactant 3

HCID 11534BromoacetonitrileHCID 81531DiisopropylethylamineHCID 8172085-amino-2-bromobenzonitrile

Product 1

HCID 86613167HCID 86613167, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
100 °C

Procedure

Mix 5-amino-2-bromobenzonitrile (0.76 mmol) in anhydrous THF (3 ml), N,N-diisopropylethylamine (0.92 mmol), and bromoacetonitrile (1.0 mmol) at room temperature under inert atmosphere. Heat the mixture to 100° C. for 16 h in a sealed tube. Cool in ice bath, filter the precipitate and evaporate the filtrate to dryness to afford a crude residue. Purify by flash chromatography (Silica gel-CHCl3/Ethanol/NH4OH 9:1:0.1) to yield the title compound.

Workup

  1. temperatureCool in ice bath
  2. filtrationfilter the precipitate
  3. customevaporate the filtrate to dryness
  4. customto afford a crude residue
  5. customPurify by flash chromatography (Silica gel-CHCl3/Ethanol/NH4OH 9:1:0.1)

Sources & evidence

ORD record
ord-9db4380ff0ae4557a0aa881d69f64b9a
Source dataset
uspto-grants-2008_07
Patent number
US07393868B2

Reaction notes

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