2-Fluoro-5-methylphenyl isocyanate → 1-[4-(3-Chloro-4-cyanoisothiazol-5-yl)phenyl]-3-(2-fluoro-5-methylphenyl)urea

HRID 871003ノート

反応式

HRID 871003 の反応式
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:12][N:11]=[C:10]([Cl:13])[C:9]=2[C:14]#[N:15])=[CH:4][CH:3]=1.[F:16][C:17]1[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][C:18]=1[N:24]=[C:25]=[O:26]>C1COCC1>[Cl:13][C:10]1[C:9]([C:14]#[N:15])=[C:8]([C:5]2[CH:4]=[CH:3][C:2]([NH:1][C:25]([NH:24][C:18]3[CH:19]=[C:20]([CH3:23])[CH:21]=[CH:22][C:17]=3[F:16])=[O:26])=[CH:7][CH:6]=2)[S:12][N:11]=1

参加物

4

反応物 2

HCID 27333772-Fluoro-5-methylphenyl isocyanate2 回HCID 866892235-(4-Aminophenyl)-3-chloroisothiazole-4-carbonitrile

生成物 1

HCID 866892241-[4-(3-Chloro-4-cyanoisothiazol-5-yl)phenyl]-3-(2-fluoro-5-methylphenyl)urea収率 90.3%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A solution of 5-(4-Aminophenyl)-3-chloroisothiazole-4-carbonitrile (4.565 g, 19.4 mmol) and 2-fluoro-5-methylphenyl isocyanate (5.85 g, 38.7 mmol) in 100 mL of dry THF was heated to reflux overnight. TLC indicated presence of considerable amount of starting material. Additional 2 g of 2-fluoro-5-methylphenyl isocyanate was added and the reaction was continued for another 24 h. The reaction was cooled to RT. THF was removed in vacuo and the resulting solid was stirred in 200 mL of Et2O for 1 h. Product was collected by filtration and washed with Et2O/hexanes to afford a light yellow solid (6.78 g, 90%).

後処理

  1. temperatureto reflux overnight
  2. customTHF was removed in vacuo
  3. filtrationProduct was collected by filtration
  4. washwashed with Et2O/hexanes

出典と根拠

ORDレコード
ord-2aaff343e1904d1aa8c5501c749b9629
出典データセット
uspto-grants-2015_03
特許番号
US08969583B2

反応ノート

読み込み中…