Dimethylformamide → HCID 178421234, compound

HRID 231253Notes

Reaction equation

[CH3:1][C:2]12[C:8]([CH3:10])([CH3:9])[C:5]([C:11]([NH:13][C:14]3[CH:19]=[CH:18][C:17]([CH2:20][C:21]#[N:22])=[CH:16][CH:15]=3)=[O:12])([CH2:6][CH2:7]1)[O:4][C:3]2=[O:23].[N-:24]=[N+:25]=[N-:26].[Na+].[Cl-].[NH4+].CN(C)C=O>[Cl-].[Na+].O.O>[CH3:1][C:2]12[C:8]([CH3:9])([CH3:10])[C:5]([C:11]([NH:13][C:14]3[CH:19]=[CH:18][C:17]([CH2:20][C:21]4[NH:26][N:25]=[N:24][N:22]=4)=[CH:16][CH:15]=3)=[O:12])([CH2:6][CH2:7]1)[O:4][C:3]2=[O:23]

Participants

Conditions

Temperature: 135 °C

Procedure

4,7,7-Trimethyl-3-oxo-N-[4-(cyanomethyl)phenyl]-2-oxabicyclo[2.2.1]-heptane-1-carboxamide (6 g, prepared in the preceding paragraph), sodium azide (6.24 g), ammonium chloride (5.1 g) and dimethylformamide (100 mL) were heated in a 135° C. oil bath for 20 hours under a nitrogen atmosphere. Water was added to the hot mixture until homogeneity was achieved. The mixture was then cooled to room temperature, poured onto saturated brine solution in a separatory funnel, and extracted with ethyl acetate. The extracts were washed with saturated brine solution, dried over MgSO4 and concentrated in a rotary evaporator. The crude product was dissolved in hot acetone, then cooled in a 0° C. freezer to yield 4.1 g. (60% yield) of the title compound as a dark yellow solid; m.p. 224°-225° C. (dec.).

Workup

temperatureThe mixture was then cooled to room temperature
extractionextracted with ethyl acetate
washThe extracts were washed with saturated brine solution
dry with materialdried over MgSO4
concentrationconcentrated in a rotary evaporator
dissolutionThe crude product was dissolved in hot acetone
temperaturecooled in a 0° C. freezer
customto yield 4.1 g

Sources & evidence

ORD record: ord-9769fff1bdde44a3a2bc313aba049ee5
Source dataset: uspto-grants-1989_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04845231

Reaction notes

Loading…