p-Isopropylphenyl isocyanate → 1-Benzylindolin-5-yl 4-isopropylphenylcarbamate

HRID 2360119Notes

Reaction equation

HRID 2360119 reaction equation
[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([OH:17])=[CH:14][CH:15]=2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Na].[CH:19]([C:22]1[CH:27]=[CH:26][C:25]([N:28]=[C:29]=[O:30])=[CH:24][CH:23]=1)([CH3:21])[CH3:20]>C(OCC)C>[CH:19]([C:22]1[CH:27]=[CH:26][C:25]([NH:28][C:29](=[O:30])[O:17][C:13]2[CH:12]=[C:11]3[C:16](=[CH:15][CH:14]=2)[N:8]([CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH2:9][CH2:10]3)=[CH:24][CH:23]=1)([CH3:21])[CH3:20]

Participants

5

Reactant 3

HCID 94416p-Isopropylphenyl isocyanateHCID 5360545SodiumHCID 866598571-Benzylindolin-5-ol

Product 1

HCID 468661431-Benzylindolin-5-yl 4-isopropylphenylcarbamateYield 87%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 1-benzylindolin-5-ol (1.50 g, 6.66 mmol) in 33 mL of diethyl ether (5 mL/mmol) 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, 4-isopropylphenylisocyanate (1.3 mL, 8.0 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=90/10 to 0/100) to obtain the title compound (2.24 g, 87%) as a white 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=90/10 to 0/100)

Sources & evidence

ORD record
ord-76f030f2c441407ea9c58e30aa976ea8
Source dataset
uspto-grants-2014_04
Patent number
US08686024B2

Reaction notes

Loading…