Hydrogen Peroxide → HCID 15702811, compound

HRID 2073204Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]([C:8]2[N:18]3[C:19]4[N:11]([C:12](=S)[NH:13][C:14](=[O:20])[C:15]=4[CH:16]=[N:17]3)[CH2:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1.[OH-].[Na+].OO.[CH2:26]([NH2:30])[CH:27]([CH3:29])[CH3:28]>CN(C)C=O>[F:1][C:2]1[CH:3]=[C:4]([C:8]2[N:18]3[C:19]4[N:11]([C:12]([NH:30][CH2:26][CH:27]([CH3:29])[CH3:28])=[N:13][C:14](=[O:20])[C:15]=4[CH:16]=[N:17]3)[CH2:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution or 3.00 g of 8-(3-fluorophenyl)-4,5-dihydro-5-thioxo-3H,6H-1,4,5a,8a-tetraazaacenaphthylen-3-one (Example 10) in 60.0 ml of N,N-dimethylformamide was added 10 ml of 1N sodium hydroxide. The reaction mixture was cooled to 0° C. in an ice bath, then 3.40 ml of 30% hydrogen peroxide was added to the mixture dropwise. The reaction mixture was stirred at 0° C. for 30 minutes, then 6.0 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 by filtration, washed with water, then ether to give 1.24 g of the desired product as a white solid, m.p. 256°-259° C. Following the procedure of Example 52 and reacting 8-(3-fluorophenyl)-4,5-dihydro-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 53-57 were obtained as set forth in Table VI.

Workup

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

Sources & evidence

ORD record: ord-fa5831d6ffd54a2cafea85cb4c214853
Source dataset: uspto-grants-1990_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04916137

Reaction notes

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