Sodium Hydroxide → 6'-Amino-3',4'-dihydrospiro[imidazolidine-4,2'(1'H)-naphthalene]-2,5-dione

HRID 2353264Notes

Reaction equation

C([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[CH2:10][C:9]1([C:17](=[O:18])[NH:16][C:15](=[O:19])[NH:14]1)[CH2:8][CH2:7]2)(O)=O.[N-:20]=[N+]=[N-].[Na+].[OH-].[Na+]>OS(O)(=O)=O>[NH2:20][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[CH2:10][C:9]1([C:17](=[O:18])[NH:16][C:15](=[O:19])[NH:14]1)[CH2:8][CH2:7]2

Participants

Conditions

Temperature: 50 °C

Procedure

A stirred mixture of (±)-6′-carboxy-3′,4′-dihydro-1′H-spiro[imidazolidine-4,2′-naphthalene]-2,5-dione (described in Intermediate 1) (1.50 g, 5.76 mmol), and sodium azide (749 mg, 11.53 mmol) in conc. H2SO4 (30 mL) was heated to 50° C. for 2 h, then allowed to cool to ambient temperature. The mixture was adjusted to pH 8 by addition of 6 N aqueous NaOH and concentrated in vacuo to precipitate a solid. The precipitate was collected by filtration and washed extensively with H2O. Drying in vacuo afforded the title compound as a light brown solid. MS: m/z=232 (M+1).

Workup

temperatureto cool to ambient temperature
concentrationconcentrated in vacuo
customto precipitate a solid
filtrationThe precipitate was collected by filtration
washwashed extensively with H2O
customDrying in vacuo

Sources & evidence

ORD record: ord-4c08b0425d2f43038cd7af017bf299d7
Source dataset: uspto-grants-2010_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07750010B2

Reaction notes

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