Hydrogen Peroxide → HCID 86089939, compound

HRID 1981097Notes

Reaction equation

COC([N:5]1[N:12](C(OC)=O)[CH:11]2[CH:6]1[CH:7]1[CH:17]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])[CH:10]2[CH:9]=[CH:8]1)=O.[OH-].[K+].OO>CO>[C:19]([O:18][CH:17]1[CH:7]2[CH:8]=[CH:9][CH:10]1[CH:11]1[CH:6]2[N:5]=[N:12]1)([CH3:22])([CH3:20])[CH3:21]

Participants

Conditions

Temperature: 20 °C

Procedure

50 parts of 3,4-dimethoxycarbonyl-9-t-butoxy-3,4-diazatricyclo[4,2,1,02,5 ]non-7-ene, 50 parts of KOH and 250 parts of methanol were refluxed for 7 hours, after which 36 parts of 30 percent strength aqueous H2O2 were added dropwise at 60° C. and stirring was continued for a further hour at 60° C. The mixture was cooled to 20° C., and thereafter the solid product was filtered off under suction and washed with 50 parts of methanol, the combined filtrates were evaporated down in a rotary evaporator at from 20° to 40° C. and under 20 mbar, and the residue was extracted in a soxhlet for 12 hours with 300 parts of petroleum ether. The petroleum ether phase was evaporated down to give 28.5 parts (93 mole %) of 9-t-butoxy-3,4-diazatricyclo[4,2,1,02,5 ]nona-3,7-diene of melting point 78° C. (from naphtha). ##STR14##

Workup

waitwas continued for a further hour at 60° C
filtrationthe solid product was filtered off under suction
washwashed with 50 parts of methanol
customthe combined filtrates were evaporated down in a rotary evaporator at from 20° to 40° C. and under 20 mbar
extractionthe residue was extracted in a soxhlet for 12 hours with 300 parts of petroleum ether
customThe petroleum ether phase was evaporated down

Sources & evidence

ORD record: ord-7090b80694194492b4a211395f0a33d1
Source dataset: uspto-grants-1985_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04512795

Reaction notes

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