反応 #943

反応方程式

2-fluoro-6-[(3-methyl-5-methoxyphenyl)sulfonyl]benzonitrile

2-Fluoro-6-[(3 -methyl-5-methoxyphenyl)sulfonyl]benzonitrile

ammonia

→

2-amino-6-[(3-methyl-5-methoxyphenyl)sulfonyl]benzonitrile

収率 34.0%

溶媒

ethanol

THF

反応条件

後処理

1. 1
   その他The solvent was removed in vacuo
2. 2
   workup.ADDITION20 mL of 1 NaOH was added
3. 3
   抽出This aqueous solution was extracted with 3×50 mL of EtOAc
4. 4
   乾燥The EtOAc solution was dried over MgSO4
5. 5
   その他After solvent removal
6. 6
   その他the crude product was recrystallized from absolute ethanol

実験手順

A solution of 0.3 g (0.00098 mol) of 2-fluoro-6-[(3-methyl-5-methoxyphenyl)sulfonyl]benzonitrile (Example 25) in 10 mL of absolute ethanol and ca. 2 mL of THF was saturated with ammonia. The resultant solution was sealed in a glass-lined Parr bomb and heated to 130° C. for 4 h. The solvent was removed in vacuo. 20 mL of 1 NaOH was added. This aqueous solution was extracted with 3×50 mL of EtOAc. The EtOAc solution was dried over MgSO4. After solvent removal, the crude product was recrystallized from absolute ethanol to give 0.1 g (34%) of 2-amino-6-[(3-methyl-5-methoxyphenyl)sulfonyl]benzonitrile: mp 166°-168° C.; NMR (Me2SO-d6, 200 MHz δ 2.4 (s, 3H), 3.87 (s, 3H), 6.7 (br s, 2H), 7.13 (apparent d, 1H), 7.2 (unresolved s, 1H), 7.3-7.5 (m, 2H), 7.57 (apparent t, 1H). Anal. Calc. for C15H14N2O3S: C, 59.59; H, 4.67;N, 9.27; S, 10.6. Found: C, 59.67;H, 4.71;N, 9.25; S, 10.51.

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