Nitrogen → HCID 86747551, compound

HRID 1974673Notes

Reaction equation

[NH2:1][C:2]1[C:34]([C:35]#[N:36])=[N:33][C:5]2[CH:6]=[C:7]3[C:16](=[N:17][C:4]=2[CH:3]=1)[C:15]1[N:14]=[C:13]2[C:18](=CC4C=CC=CC=4)[CH2:19][CH2:20][CH2:21][C:12]2=[C:11]([CH2:29][CH2:30][CH2:31][CH3:32])[C:10]=1[CH2:9][CH2:8]3.N#N.[O:39]=[O+][O-].CSC>CO>[NH2:1][C:2]1[C:34]([C:35]#[N:36])=[N:33][C:5]2[CH:6]=[C:7]3[C:16](=[N:17][C:4]=2[CH:3]=1)[C:15]1[N:14]=[C:13]2[C:18](=[O:39])[CH2:19][CH2:20][CH2:21][C:12]2=[C:11]([CH2:29][CH2:30][CH2:31][CH3:32])[C:10]=1[CH2:9][CH2:8]3

Participants

Conditions

Temperature: -78 °C

Procedure

To a 250 mL round bottomed flask were added 0.305 g (0.147 mmol) of crude 2-amino-12-benzylidene-8-n-butyl-3-cyano-6,7,9,10,11,12hexahydrobenzo[b]pyrido[2,3-j][1,10]phenanthroline, 40 mL of CH2CL2 and 115 mL of CH3OH. The solution was cooled to approximately -78° C. by means of a dry ice/acetone bath and N2 was passed through the solution for 5 min. A stream of O3 was passed through the solution until the color turned from dark orange-brown to dark green-brown. N2 was passed through the solution for an additional 5 min. then 0.6 mL of dimethyl sulfide was added via syringe. The solution was allowed to warm to room temperature overnight and the solvents removed by rotary evaporation. The crude product was washed with ether (3×50 mL) then recrystallized from CHCL3 /EtOH. Vacuum filtration gave 0.09 g (35%) of product as a yellow solid after drying at 0.5 mm Hg pressure and 61° C. for 48 hr. (mp>300° C.).

Workup

temperatureto warm to room temperature overnight
customthe solvents removed by rotary evaporation
washThe crude product was washed with ether (3×50 mL)
customthen recrystallized from CHCL3 /EtOH
filtrationVacuum filtration

Sources & evidence

ORD record: ord-a182bbdf5eb04f639a1b9443bdc9abc3
Source dataset: uspto-grants-1994_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05283333

Reaction notes

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