Diethyl Ether → 6-Nitro-9-(thiophene-2-sulfonyl)-1,4,7,8,9,10-hexahydro-pyrido[3,4-f]quinoxaline-2,3-dione

HRID 1739676Notes

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].Cl[S:21]([C:24]1[S:25][CH:26]=[CH:27][CH:28]=1)(=[O:23])=[O:22].C(N(CC)CC)C.C(OCC)C>C1COCC1.CN(C=O)C>[N+:1]([C:4]1[C:17]2[CH2:16][CH2:15][N:14]([S:21]([C:24]3[S:25][CH:26]=[CH:27][CH:28]=3)(=[O:23])=[O:22])[CH2:13][C:12]=2[C:11]2[NH:10][C:9](=[O:18])[C:8](=[O:19])[NH:7][C:6]=2[CH:5]=1)([O-:3])=[O:2]

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of the 6-nitropyridoquinoxalinedione (0.1 g, 0.38 mmol), 2-chlorosulfonyl thiophene (104 mg, 0.57 mmol), triethylamine (70 μl) in THF (5 mL) and DMF (5 mL) was stirred at 60° C. for 24 hours. The mixture was poured onto water and diethyl ether. The precipitate was collected by filtration, washed with water and ether, and dried in vacuo to give product as a yellow solid (80 mg) in 52% yield; mp >300° C. m/e, M+1 409 nmR, IR, CHN.

Workup

filtrationThe precipitate was collected by filtration
washwashed with water and ether
customdried in vacuo

Sources & evidence

ORD record: ord-f8d22c6dac5d41ce86ba8e324e8b06f6
Source dataset: uspto-grants-1999_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05968928

Reaction notes

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