3,4-Diaminobenzonitrile → HCID 11598923, compound

HRID 730241Notes

Reaction equation

[C:1]([C:3]1[CH:4]=[C:5]([NH2:10])[C:6]([NH2:9])=[CH:7][CH:8]=1)#[N:2].[S:11]1[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=2[CH:13]=[C:12]1[S:20](Cl)(=[O:22])=[O:21]>N1C=CC=CC=1.C(OCC)(=O)C>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([NH:9][S:20]([C:12]2[S:11][C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=3[CH:13]=2)(=[O:22])=[O:21])=[C:5]([NH:10][S:20]([C:12]2[S:11][C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=3[CH:13]=2)(=[O:21])=[O:22])[CH:4]=1)#[N:2]

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 4-cyanobenzene-1,2-diamine (1 mmol) in pyridine (4 mL), benzothiophene-2-sulfonyl chloride (2.2 mmol) was added in small portions. The reaction mixture was then heated at 80° C. with stirring until the reaction was complete as determined by TLC or LC-MS. The reaction mixture was then diluted with ethyl acetate (20 mL). The organic phase was washed with 10% aqueous HCl solution (15 mL), water (15 mL) and brine (5 mL). The organic phase was dried over anhydrous sodium sulfate and concentrated under vacuum. The residue obtained was purified by flash column chromatography eluting with DCM/EtOAc to obtain 184 mg of N,N′-(4-cyano-1,2-phenylene)bis(1-benzothiophene-2-sulfonamide) as a solid.

Workup

washThe organic phase was washed with 10% aqueous HCl solution (15 mL), water (15 mL) and brine (5 mL)
dry with materialThe organic phase was dried over anhydrous sodium sulfate
concentrationconcentrated under vacuum
customThe residue obtained
customwas purified by flash column chromatography
washeluting with DCM/EtOAc

Sources & evidence

ORD record: ord-b3fa5100e04c4ca091168d739ec885a4
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07582673B2

Reaction notes

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