Butyl isocyanate → HCID 58087441, compound

HRID 1261052Notes

Reaction equation

HRID 1261052 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-ba0d1066273542afaa246cf72e4c43a7
Source dataset
uspto-grants-2013_06
Patent number
US08470818B2

Reaction notes

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