Ammonium Hydroxide → 2-Amino-6-[(3-methoxyphenyl)sulfonyl]benzonitrile

HRID 838

反応式

HRID 838 の反応式
F[C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([S:10]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH3:20])[CH:14]=2)(=[O:12])=[O:11])[C:3]=1[C:4]#[N:5].[NH4+:21].[OH-]>CO.CCO>[NH2:21][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([S:10]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH3:20])[CH:14]=2)(=[O:12])=[O:11])[C:3]=1[C:4]#[N:5]

参加物

4

反応物 2

HCID 14923Ammonium HydroxideHCID 105825402-Fluoro-6-[(3-methoxyphenyl)sulfonyl]benzonitrile

生成物 1

HCID 4834502-Amino-6-[(3-methoxyphenyl)sulfonyl]benzonitrile

試薬・触媒・溶媒 1

HCID 18681192Ethanol, mixt. with methanol溶媒

反応条件

温度
130 °C

実験手順

To a solution of 0.7 g (2.4 mmol) of 2-fluoro-6-[(3-methoxyphenyl)sulfonyl]benzonitrile (Example 14) in 110 ml of MeOH/EtOH (7:4) was added 20 mL of concentrated NH4OH, This mixture was sealed in a glass-lined bomb and heated at 130° C. for 3 h. After solvent removal, the resultant concentrate was purified by flash column chromatography on silica gel with 5% MeOH in methylene chloride as the eluent. This resulted in 0.16 g (23%) of 2-amino-6-[(3-methoxyphenyl)sulfonyl]benzonitrile as a solid: mp 186°-191° C.; NMR (Me2SO-d6, 200MHz) δ 3.82 (s, 3H), 6.6 (br s, 2H), 7.1 (apparent d, 1H), 7.2-7.7 (m, 6H); mass spec (CI) 289 (M+ +1, 100%). Anal. Calc. for C14H12N2 O3S: C, 58.32; H, 4.20;N, 9.72; S, 11.12. Found: C, 58.13; H, 4.17; N, 9.51; S, 10.95.

後処理

  1. customThis mixture was sealed in a glass-lined bomb
  2. customAfter solvent removal
  3. concentrationthe resultant concentrate
  4. customwas purified by flash column chromatography on silica gel with 5% MeOH in methylene chloride as the eluent
  5. customThis resulted in 0.16 g (23%) of 2-amino-6-[(3-methoxyphenyl)sulfonyl]benzonitrile as a solid

出典と根拠

ORDレコード
ord-70d2fe8819214856a573963ea6b87bb1
出典データセット
uspto-grants-1998_03
特許番号
US05723452

関連ノート

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