Hexyl isocyanate → HCID 46865283, compound

HRID 2360161Notes

Reaction equation

HRID 2360161 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][N:8]1[C:16]2[C:11](=[CH:12][C:13]([OH:17])=[CH:14][CH:15]=2)[CH2:10][CH2:9]1.[Na].[CH2:19]([N:25]=[C:26]=[O:27])[CH2:20][CH2:21][CH2:22][CH2:23][CH3:24]>C(OCC)C>[CH2:19]([NH:25][C:26](=[O:27])[O:17][C:13]1[CH:12]=[C:11]2[C:16](=[CH:15][CH:14]=1)[N:8]([CH2:7][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=1)[CH2:9][CH2:10]2)[CH2:20][CH2:21][CH2:22][CH2:23][CH3:24]

Participants

5

Reactant 3

HCID 75659Hexyl isocyanateHCID 5360545SodiumHCID 86659882HCID 86659882, compound

Product 1

HCID 46865283HCID 46865283, compoundYield 68.2%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 1-(2-pyridylmethyl)indolin-5-ol (20 mg, 88 μmol) in 0.5 mL of diethyl ether was added a piece of sodium (1 mg to 10 mg) at room temperature. After the reaction mixture was stirred at the same temperature for 2 min, n-hexylisocyanate (15 μL, 0.11 mmol, 1.2 equivalent) was added with additional stirring for 5 min to 10 min. After removal of sodium, the filtrate was concentrated in vacuo, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate=80/20 to 30/70) to obtain the title compound (21.2 mg, 68%) as a slightly brown solid.

Workup

  1. stirringwith additional stirring for 5 min to 10 min
  2. customAfter removal of sodium
  3. concentrationthe filtrate was concentrated in vacuo
  4. customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate=80/20 to 30/70)

Sources & evidence

ORD record
ord-73519c44f89348e697b026df4a08814c
Source dataset
uspto-grants-2014_04
Patent number
US08686024B2

Reaction notes

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