Sodium Hydroxide → 5-Phenyl-2-(2-hydroxy-3-phenyl-5-tert-octylphenyl)-2H-benzotriazole

HRID 1375292ノート

反応式

HRID 1375292 の反応式
[OH-].[Na+].[OH:3][C:4]1[C:9]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:8][C:7]([C:16]([CH2:19][C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:18])[CH3:17])=[CH:6][C:5]=1[N:24]=[N:25][C:26]1[CH:31]=[CH:30][C:29]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)=[CH:28][C:27]=1[N+:38]([O-])=O>O>[C:32]1([C:29]2[CH:30]=[CH:31][C:26]3=[N:25][N:24]([C:5]4[CH:6]=[C:7]([C:16]([CH2:19][C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:18])[CH3:17])[CH:8]=[C:9]([C:10]5[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=5)[C:4]=4[OH:3])[N:38]=[C:27]3[CH:28]=2)[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1

参加物

4

反応物 2

HCID 14798Sodium HydroxideHCID 1363776762-Hydroxy-2'nitro3,4'-diphenyl-5-tert-octylazobenzene2 回

生成物 1

HCID 235012165-Phenyl-2-(2-hydroxy-3-phenyl-5-tert-octylphenyl)-2H-benzotriazole

試薬・触媒・溶媒 1

HCID 962Water溶媒2 回

実験手順

To a solution of sodium hydroxide (6 g, 0.15 mol) in 8 mL of water is added 2-hydroxy-2′nitro3,4′-diphenyl-5-tert-octylazobenzene (6.56 g), prepared in (D) above. The reaction mixture is heated to reflux and then formadine sulfinic acid (10.8 g, 0.1 mol) is added portionwise over 20 minutes. The reaction mixture is heated at reflux for 1.5 hours. To the cooled reaction mixture is added 200 mL of water and the ethanol is removed under vacuum. The reaction mixture is adjusted to pH 4 with hydrochloric acid. The resultant mixture is extracted twice with methylene chloride and the combined organic phases are extracted with water. The organic phase is dried over anhydrous magnesium sulfate, and the solvent is then removed under vacuum. The residue is recrystallized sequentially from a mixture of water and methanol, and petroleum ether to give the title compound as a white solid melting at 123–125° C.

後処理

  1. temperatureThe reaction mixture is heated
  2. temperatureto reflux
  3. temperatureThe reaction mixture is heated
  4. temperatureat reflux for 1.5 hours
  5. customTo the cooled reaction mixture
  6. customthe ethanol is removed under vacuum
  7. extractionThe resultant mixture is extracted twice with methylene chloride
  8. extractionthe combined organic phases are extracted with water
  9. dry with materialThe organic phase is dried over anhydrous magnesium sulfate
  10. customthe solvent is then removed under vacuum
  11. customThe residue is recrystallized sequentially from a mixture of water and methanol, and petroleum ether

出典と根拠

ORDレコード
ord-9cb34de7dfca4adfbe2b1c602986a07e
出典データセット
uspto-grants-2007_01
特許番号
US07166659B2

反応ノート

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