Ammonia → 2-Amino-6-(3,5-dimethylphenyl)sulfonylbenzonitrile

HRID 844

Reaktionsgleichung

[CH3:1][C:2]1[CH:3]=[C:4]([S:9]([C:12]2[CH:19]=[CH:18][CH:17]=[C:16](F)[C:13]=2[C:14]#[N:15])(=[O:11])=[O:10])[CH:5]=[C:6]([CH3:8])[CH:7]=1.[NH3:21].CCOC(C)=O>CO>[NH2:21][C:16]1[CH:17]=[CH:18][CH:19]=[C:12]([S:9]([C:4]2[CH:3]=[C:2]([CH3:1])[CH:7]=[C:6]([CH3:8])[CH:5]=2)(=[O:11])=[O:10])[C:13]=1[C:14]#[N:15]

Komponenten

Reaktionsbedingungen

Temperatur: -78 °C

Versuchsvorschrift

2-[(3,5-Dimethylphenyl)sulfonyl]-6-fluorobenzonitrile (Example 20) (0.5 g 1.7 mmol) was dissolved in 80 ml of methanol and chilled to -78° C. Condensed ammonia (20 ml, 15.4 g, 905 mmol) was added and the mixture was heated to150° C. in a sealed Parr bomb for 24 h. Chromatography on silica gel (flash; Hex/EtOAc 1:1) provided 0.28 g (56%) of 2-amino-6-[(3,5-dimethylphenyl)sulfonyl]benzonitrile: mp 208°-209° C.;; NMR (Me2SO-d6, 200 MHz) δ 2.36 (s, 6H), 6.59 (br s, 2H), 7.10 (apparent d, 1H), 7.3-7.4 (m, 2H) 7.54 (apparent d, 1H), 7.58 (m, 2H); mass spec (CI) M+ +1=287. Anal. Calc. for C15H14N2O2S: C, 62.92; H, 4.93; N: 9.78; S, 11.20. Found: C, 63.02; H, 4.98; N, 9.72; S, 11.12.

Aufarbeitung

additionwas added
temperaturethe mixture was heated to150° C

Quellen und Nachweise

ORD-Eintrag: ord-b5f73f3ea0a54afca47617c9e6b59c43
Quelldatensatz: uspto-grants-1998_03
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US05723452

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