Triethylamine → 1-(3-nitro-phenyl)-3-(2-oxo-2,3-dihydro-1H-indol-6-yl)-urea

HRID 422010Notes

Reaction equation

HRID 422010 reaction equation
[NH2:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][C:7](=[O:11])[NH:8]2)=[CH:4][CH:3]=1.C(N(CC)CC)C.[N:19]([C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([N+:28]([O-:30])=[O:29])[CH:23]=1)=[C:20]=[O:21]>C1COCC1>[N+:28]([C:24]1[CH:23]=[C:22]([NH:19][C:20]([NH:1][C:2]2[CH:10]=[C:9]3[C:5]([CH2:6][C:7](=[O:11])[NH:8]3)=[CH:4][CH:3]=2)=[O:21])[CH:27]=[CH:26][CH:25]=1)([O-:30])=[O:29]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 768353-Nitrophenyl isocyanateHCID 5905386-Amino-1,3-dihydro-2H-indol-2-one

Product 1

HCID 598042911-(3-nitro-phenyl)-3-(2-oxo-2,3-dihydro-1H-indol-6-yl)-urea

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 6-amino-1,3-dihydro-indol-2-one (0.15 g, 1.0 mmol) and triethylamine (0.30 g, 3.0 mmol) in THF (10 ml) is added 1-isocyanato-3-nitro-benzene (0.16 g, 1.0 mmol). The reaction is stirred at room temperature for 1 hour and the precipitate is collected by vacuum filtration and washed with ethanol to give the desired compound as a light yellow solid. LC-MS: 313.1 (MH+).

Workup

  1. filtrationthe precipitate is collected by vacuum filtration
  2. washwashed with ethanol

Sources & evidence

ORD record
ord-3fb6933e45c34b63b5d2d4dd63befc29
Source dataset
uspto-grants-2012_01
Patent number
US08101608B2

Reaction notes

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