4-Chloro-2-methylphenyl isocyanate → N-(4-chloro-2-methylphenyl)isoindoline-2-carboxamide

HRID 1644121Notes

Reaction equation

HRID 1644121 reaction equation
[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][NH:2]1.[Cl:10][C:11]1[CH:16]=[CH:15][C:14]([N:17]=[C:18]=[O:19])=[C:13]([CH3:20])[CH:12]=1>O1CCOCC1>[Cl:10][C:11]1[CH:16]=[CH:15][C:14]([NH:17][C:18]([N:2]2[CH2:3][C:4]3[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=3)[CH2:1]2)=[O:19])=[C:13]([CH3:20])[CH:12]=1

Participants

4

Reactant 2

HCID 1421574-Chloro-2-methylphenyl isocyanateHCID 422478Isoindoline

Product 1

HCID 57527884N-(4-chloro-2-methylphenyl)isoindoline-2-carboxamideYield 94.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of isoindoline (238 mg, 2.0 mmol) in dry 1,4-dioxane (10 mL) was added 4-chloro-2-methylphenyl isocyanate (335 mg, 2.0 mmol) under argon at room temperature. The reaction mixture was then stirred at RT overnight. The solvent was evaporated under reduced pressure, and the residue was purified by recrystallization from ethanol to give the title compound (540 mg, 94%) as a white solid. 1H NMR (500 MHz, DMSO-d6): δ 2.24 (s, 2H), 4.76 (s, 4H), 7.20 (dd, J=2.5, 8.5 Hz, 1H), 7.27 (d, J=2.5 Hz, 1H), 7.30-7.32 (m, 2H), 7.34-7.37 (m, 2H), 7.42 (d, J=8.5 Hz, 1H), 7.84 (s, 1H); 13C NMR (DMSO-d6): δ 17.7, 51.9, 122.8, 125.6, 126.8, 127.3, 128.1, 129.5, 134.7, 136.8, 154.2; MS (MH+, 287); EA calc'd for C16H15ClN2O: C, 67.02; H, 5.27; N, 9.77. Found C, 66.82; H, 5.41; N, 9.92.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. customthe residue was purified by recrystallization from ethanol

Sources & evidence

ORD record
ord-083ec49ed21a4f439b43738b1096d27e
Source dataset
uspto-grants-2012_02
Patent number
US08124121B2

Reaction notes

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