Phenyl Isothiocyanate → 6-Nitro2,3-dioxo-1,2,3,4,7,10-hexahydro-8H-pyrido[3,4-f]quinoxaline-9-carbothioic Acid Phenylamide

HRID 1739675Notes

Reaction equation

[N+:1]([C:4]1[C:13]2[N:14]=[CH:15][CH:16]=[CH:17][C:12]=2[C:11]2[C:6](=[N:7][C:8](=[O:19])[C:9](=[O:18])[N:10]=2)[CH:5]=1)([O-:3])=[O:2].[C:20]1([N:26]=[C:27]=[S:28])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C(N(CC)CC)C>CN(C=O)C>[C:20]1([NH:26][C:27]([N:14]2[CH2:15][CH2:16][C:17]3[C:4]([N+:1]([O-:3])=[O:2])=[CH:5][C:6]4[NH:7][C:8](=[O:19])[C:9](=[O:18])[NH:10][C:11]=4[C:12]=3[CH2:13]2)=[S:28])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of the 6-nitropyridoquinoxalinedione (0.1 g, 0.38 mmol), phenylisothiocyanate (70 μL), triethylamine (70 μL) in DMF (5 mL) was stirred at 60° C. for 24 hours. The mixture was poured onto water and allowed to stand. The precipitate was collected by filtration, washed with water and ether, and dried in vacuo to give product (130 mg) as a beige solid; mp 270-274° C., nmR, IR.

Workup

additionThe mixture was poured onto water
filtrationThe precipitate was collected by filtration
washwashed with water and ether
customdried in vacuo

Sources & evidence

ORD record: ord-14f3f6e8517d4040b4b7d4ed5cd21ce1
Source dataset: uspto-grants-1999_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05968928

Reaction notes

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