Reaction #940

Reaction equation

EtOAc

2-[(3,5-Dimethylphenyl)sulfonyl]-6-fluorobenzonitrile

2-[(3,5-dimethylphenyl)sulfonyl]-6-fluorobenzonitrile

ammonia

→

2-amino-6-[(3,5-dimethylphenyl)sulfonyl]benzonitrile

Yield 57.5%

Solvents

methanol

Conditions

Workup

1. 1
   workup.ADDITIONwas added
2. 2
   Temperaturethe mixture was heated to150° C

Procedure

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.

Source