Hydrogen Peroxide → 5-[(2-Methylpropyl)amino]-8-phenyl-3H,6H-1,4,5a,8a-tetraazaacenaphthylen-3-one

HRID 2073203Notes

Reaction equation

[C:1]1([C:7]2[N:17]3[C:18]4[N:10]([C:11](=S)[NH:12][C:13](=[O:19])[C:14]=4[CH:15]=[N:16]3)[CH2:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+].OO.[CH2:25]([NH2:29])[CH:26]([CH3:28])[CH3:27]>CN(C)C=O>[CH3:27][CH:26]([CH3:28])[CH2:25][NH:29][C:11]1[N:10]2[C:18]3[N:17]([C:7]([C:1]4[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=4)=[CH:8][CH2:9]2)[N:16]=[CH:15][C:14]=3[C:13](=[O:19])[N:12]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 500 mg of 4,5-dihydro-8-phenyl-5-thioxo-3H,6H-1,4,5a,8a-tetraazaacenaphthylen-3-one (prepared as described in Example 7) in 10.0 ml of N,N-di-methylformamide was added 1.8 ml of 1N sodium hydroxide. The reaction mixture was cooled to 0° C. in an ice bath, then 0.6 ml of 30% hydrogen peroxide was added to the mixture dropwise. The reaction mixture was stirred at 0° C. for about 30 minutes, then 1.0 ml of isobutylamine was added in one portion and the mixture was allowed to warm to room temperature, then was stirred for 2 hours. The solid was collected and washed with water, then ether to give 253 mg of the desired product as a white solid, m.p. 265°-268° C. (dec). Following the procedure of Example 44 and reacting 4,5-dihydro-8-phenyl-5-thioxo-3H,6H-1,4,5a,8a-tetraazaacenaphthylen-3-one with the appropriate primary aliphatic amine or cyclic secondary amine, the products of Examples 45-51 were obtained as set forth in Table V.

Workup

temperatureto warm to room temperature
stirringwas stirred for 2 hours
customThe solid was collected
washwashed with water

Sources & evidence

ORD record: ord-361b6c34f383458582e6676e4cb24a55
Source dataset: uspto-grants-1990_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04916137

Reaction notes

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