Potassium Carbonate → 4-[2-(4-Nitro-phenyl)-6-oxo-4-thioxo-6H-1-oxa-3b,5-diaza-cyclopenta[a]pentalen-5-yl]-butyronitrile

HRID 1713044

Reaction equation

C([O:3][C:4]([C:6]1[NH:10][C:9]2[CH:11]=[C:12]([C:14]3[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=3)[O:13][C:8]=2[CH:7]=1)=O)C.C(OC(=O)C(CC)CCN1C(=S)N2C3C=C(C4C=CC([N+]([O-])=O)=CC=4)OC=3C=C2C1=O)C.[N:55]([CH2:58][CH2:59][CH2:60][C:61]#[N:62])=[C:56]=[S:57].C([O-])([O-])=O.[K+].[K+]>C(O)C>[N+:20]([C:17]1[CH:16]=[CH:15][C:14]([C:12]2[O:13][C:8]3[CH:7]=[C:6]4[C:4](=[O:3])[N:55]([CH2:58][CH2:59][CH2:60][C:61]#[N:62])[C:56](=[S:57])[N:10]4[C:9]=3[CH:11]=2)=[CH:19][CH:18]=1)([O-:22])=[O:21]

Participants

Conditions

Temperature: 110 °C

Procedure

2-(4-nitro-phenyl)-4H-furo[3,2-b]pyrrole-5-carboxylic acid ethyl ester (60.97 mg, 0.21 mmol), prepared as described hereinabove (see, preparation of Compound 1), 4-isothiocyanato-butyronitrile (664 mg, 2.1 mmol) and a fine powder of anhydrous K2CO3 (27.6 mg, 0.2 mmol) are mixed together in a sealed tube, provided with a magnetic stirrer, and the mixture is heated at 110° C. for 2 hours. The mixture is cooled to room temperature, ethanol is added (2 ml), and the formed precipitate is filtered. The crude product is recrystallized from ethanol to give Compound 35.

Workup

customprovided with a magnetic stirrer
temperatureThe mixture is cooled to room temperature
filtrationthe formed precipitate is filtered
customThe crude product is recrystallized from ethanol

Sources & evidence

ORD record: ord-f7bf6337c3444f61a0f6334556d517b1
Source dataset: uspto-grants-2010_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07795255B2

Linked notes

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