Triethylamine → HCID 25129219, compound

HRID 339419Notes

Reaction equation

HRID 339419 reaction equation
[CH2:1]1[O:10][C:9]2[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][C:3]=2[O:2]1.Cl[C:12](OC1C=CC=CC=1)=[O:13].C(N(CC)CC)C.[CH2:28]1[C:36]2[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=2)[CH2:30][NH:29]1>C(Cl)Cl>[CH2:1]1[O:10][C:9]2[CH:8]=[CH:7][C:5]([NH:6][C:12]([N:29]3[CH2:30][C:31]4[C:36](=[CH:35][CH:34]=[CH:33][CH:32]=4)[CH2:28]3)=[O:13])=[CH:4][C:3]=2[O:2]1

Participants

6

Reactant 4

HCID 8471Triethylamine2×HCID 15891Phenyl chloroformateHCID 843101,3-Benzodioxol-5-amineHCID 422478Isoindoline

Product 1

HCID 25129219HCID 25129219, compoundYield 60.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3,4-(methylenedioxy)aniline (150 mg, 1.09 mmol) in dry DCM (4 mL) was added dropwise phenyl chloroformate (0.138 ml, 1.09 mmol) and triethylamine (0.153 ml, 1.09 mmol). After the reaction mixture was stirred at r.t for 8 hr., isoindoline (0.123 ml, 1.09 mmol) and triethylamine (0.153 ml, 1.09 mmo) were added, and the reaction mixture was stirred overnight. The solvent was then removed under reduced pressure, and the residue was purified by chromatographed on silica gel (EtOAC/Hexane: 1:3) to give the title compound (185 mg, 60%) as a white solid: m.p:165-166° C. 1H NMR (CDCl3, 500 MHz): 4.82 (s, 4H); 5.93 (s, 2H); 6.20 (s, 1H); 6.73 (s, 2H); 7.17 (s, 1H); 7.30 (m, 4H). MS (MH+, 283).

Workup

  1. stirringthe reaction mixture was stirred overnight
  2. customThe solvent was then removed under reduced pressure
  3. customthe residue was purified
  4. customby chromatographed on silica gel (EtOAC/Hexane: 1:3)

Sources & evidence

ORD record
ord-8acba4cf3dcf495fbdc39f5c844e7f1c
Source dataset
uspto-grants-2014_11
Patent number
US08895050B2

Reaction notes

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