Butyl isocyanate → HCID 58087441, compound

HRID 250596Notes

Reaction equation

HRID 250596 reaction equation
[NH:1]1[C:9]2[CH:8]=[CH:7][CH:6]=[C:5]([CH:10]=[O:11])[C:4]=2[CH:3]=[CH:2]1.[N:12]([CH2:15][CH2:16][CH2:17][CH3:18])=[C:13]=[O:14]>C(#N)C.CN(C)C1C=CN=CC=1>[CH2:15]([NH:12][C:13]([N:1]1[C:9]2[C:4](=[C:5]([CH:10]=[O:11])[CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1)=[O:14])[CH2:16][CH2:17][CH3:18]

Participants

5

Reactant 2

HCID 8110Butyl isocyanateHCID 333703Indole-4-carboxaldehyde

Product 1

HCID 58087441HCID 58087441, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6342AcetonitrileSolvent

Procedure

To 1H-Indole-4-carbaldehyde (518, 1.57 g, 10.8 mmol) in acetonitrile (20 mL) was added 1-isocyanatobutane (1.81 mL, 16.2 mmol), followed by 4-dimethylaminopyridine (130 mg, 1.1 mmol). The reaction was refluxed for 48 hours. The reaction solution was quenched with 1 M HCl (aq.) and extracted with ethyl acetate. The organic layer was washed with sodium bicarbonate and brine, dried over anhydrous magnesium sulfate, filtrated and concentrated to give a light yellow solid (519, 2.62 g, 45%). MS (ESI) [M+H+]+=245.2.

Workup

  1. temperatureThe reaction was refluxed for 48 hours
  2. customThe reaction solution was quenched with 1 M HCl (aq.)
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with sodium bicarbonate and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltrated
  7. concentrationconcentrated
  8. customto give a light yellow solid (519, 2.62 g, 45%)

Sources & evidence

ORD record
ord-9a1d3275ad9a4ee7844d81babbe50b5d
Source dataset
uspto-grants-2011_01
Patent number
US07863288B2

Reaction notes

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