Butyl isocyanate → HCID 58087441, compound

HRID 1964897Notes

Reaction equation

HRID 1964897 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 1M 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 1M 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-83bc73e8bf6c4de880d3f3ee50eb11dd
Source dataset
uspto-grants-2013_04
Patent number
US08415469B2

Reaction notes

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