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Thiophenol → 5-phenylthio-2-(2-hydroxy-3-alpha-cumyl-5-tert-octylphenyl)-2H-benzotriazole

HRID 1058100
ノート
印刷プレビュー

反応式

HRID 1058100 の反応式
Cl[C:2]1[CH:34]=[CH:33][C:5]2=[N:6][N:7]([C:9]3[CH:14]=[C:13]([C:15]([CH2:18][C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:17])[CH3:16])[CH:12]=[C:11]([C:23]([C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)([CH3:25])[CH3:24])[C:10]=3[OH:32])[N:8]=[C:4]2[CH:3]=1.CN1CCCC1=O.[OH-].[K+].[C:44]1([SH:50])[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1>O>[C:44]1([S:50][C:2]2[CH:34]=[CH:33][C:5]3=[N:6][N:7]([C:9]4[CH:14]=[C:13]([C:15]([CH2:18][C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:17])[CH3:16])[CH:12]=[C:11]([C:23]([C:26]5[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=5)([CH3:25])[CH3:24])[C:10]=4[OH:32])[N:8]=[C:4]3[CH:3]=2)[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 7969ThiophenolHCID 13387N-methyl-2-pyrrolidoneHCID 14797Potassium HydroxideHCID 218850095-chloro-2-(2-hydroxy-3-alpha-cumyl-5-tertoctylphenyl)-2H-benzotriazole

生成物 1

HCID 186728375-phenylthio-2-(2-hydroxy-3-alpha-cumyl-5-tert-octylphenyl)-2H-benzotriazole収率 94.7%

試薬・触媒・溶媒 1

HCID 962
Water
溶媒

反応条件

温度
90 °C

実験手順

To a stirred mixture of 75 g of 5-chloro-2-(2-hydroxy-3-α-cumyl-5-tert-octyl-phenyl)-2H-benzotriazole and 105 g of N-methylpyrrolidone heated at 90° C. is added first 44.3 g of 45% aqueous potassium hydroxide solution over a 15-minute period then 20.4 g of thiophenol over another 15 minutes. The reaction mixture is then heated at 170-175° C. for four hours with water being removed by distillation. After cooling to 100° C., xylene and water are added and the resultant mixture is made acidic with 15% aqueous hydrogen chloride solution. The organic layer is separated and washed with water and then concentrated. The crude product residue is recrystallized from methanol to yield 82 g of the title compound as a pale yellow solid melting at 124-125° C.

後処理

  1. customremoved by distillation
  2. temperatureAfter cooling to 100° C.
  3. additionxylene and water are added
  4. customThe organic layer is separated
  5. washwashed with water
  6. concentrationconcentrated
  7. customThe crude product residue is recrystallized from methanol

出典と根拠

ORDレコード
ord-56987e6ee35f4657853febd270ed8fb7
出典データセット
uspto-grants-2003_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06515051B2

反応ノート

読み込み中…

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