N-Hydroxyphthalimide → HCID 178515026, compound

HRID 1821827Notes

Reaction equation

HRID 1821827 reaction equation
Cl.[OH:2][CH2:3][C:4]1[N:5]=[CH:6][NH:7][CH:8]=1.O[N:10]1[C:14](=[O:15])[C:13]2=[CH:16][CH:17]=[CH:18][CH:19]=[C:12]2[C:11]1=[O:20].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1COCC1>[NH:7]1[CH:8]=[C:4]([CH2:3][O:2][N:10]2[C:14](=[O:15])[C:13]3[C:12](=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:11]2=[O:20])[N:5]=[CH:6]1

Participants

6

Reactant 4

HCID 10665N-HydroxyphthalimideHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 178418488HCID 178418488, compound

Product 1

HCID 178515026HCID 178515026, compoundYield 22%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To an ice-cold solution of 4-(hydroxymethyl)imidazole hydrochloride (2.0 g, 15 mmol), N-hydroxyphthalimide (2.4 g, 15 mmol) and triphenylphosphine (4.0 g, 15 mmol) in THF (65 mL) was added a solution of diethyl azodicarboxylate (2.6 mL, 16 mmol) in THF (10 mL) dropwise. The stirred reaction mixture was allowed to warm to ambient temperature. After 18 h, the resultant precipitate was collected by vacuum filtration. The solid was partitioned between EtOAc (75 ml) and saturated NaHCO3 (75 mL). The aqueous layer was separated and extracted again with EtOAc (75 mL). The combined organic layers were dried (Na2SO4) and concentrated under reduced pressure. Purification by column chromatography (silica gel, CH2Cl2 to 90:10 CH2Cl2/MeOH) gave 2-(1H-imidazol-4-ylmethoxy)-1,3-dihydro-2H-isoindole-1,3-dione (800 mg, 22%) as a yellow oil: 1H NMR (300 MHz, DMSO-d6) δ5.03 (2H, s), 7.30 (1H, s), 7.55 (1H, s), 7.81-7.86 (4H, m), 12.08 (1H, br s).

Workup

  1. customThe stirred reaction mixture
  2. filtrationthe resultant precipitate was collected by vacuum filtration
  3. customThe solid was partitioned between EtOAc (75 ml) and saturated NaHCO3 (75 mL)
  4. customThe aqueous layer was separated
  5. extractionextracted again with EtOAc (75 mL)
  6. dry with materialThe combined organic layers were dried (Na2SO4)
  7. concentrationconcentrated under reduced pressure
  8. customPurification by column chromatography (silica gel, CH2Cl2 to 90:10 CH2Cl2/MeOH)

Sources & evidence

ORD record
ord-10bb7cbdfb5a48d5bc052ea8fd2b6b32
Source dataset
uspto-grants-2009_10
Patent number
US07608627B2

Reaction notes

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