Sulfuric Acid → 2-(2-hydroxy-3-t-butyl-5-methylphenyl)-5-chlorobenzotriazole-N-oxide

HRID 2166257

反応式

HRID 2166257 の反応式
[N+:1]([C:4]1[CH:9]=[C:8]([Cl:10])[CH:7]=[CH:6][C:5]=1[N:11]=[N:12][C:13]1[CH:18]=[C:17]([CH3:19])[CH:16]=[C:15]([C:20]([CH3:23])([CH3:22])[CH3:21])[C:14]=1[OH:24])([O-])=O.[OH-].[Na+].C1C2C(=[O:40])C3C(=CC=CC=3)C=2C=CC=1.N(C1C=CC=CC=1)=NC1C=CC=CC=1.S(=O)(=O)(O)O>O.C(O)CCC>[OH:24][C:14]1[C:15]([C:20]([CH3:23])([CH3:22])[CH3:21])=[CH:16][C:17]([CH3:19])=[CH:18][C:13]=1[N:12]1[N+:11]([O-:40])=[C:5]2[CH:6]=[CH:7][C:8]([Cl:10])=[CH:9][C:4]2=[N:1]1

参加物

8

反応物 5

HCID 1118Sulfuric AcidHCID 2272AzobenzeneHCID 10241FluorenoneHCID 14798Sodium HydroxideHCID 89771Phenol, 2-[2-(4-chloro-2-nitrophenyl)diazenyl]-6-(1,1-dimethylethyl)-4-methyl-

生成物 1

HCID 141494702-(2-hydroxy-3-t-butyl-5-methylphenyl)-5-chlorobenzotriazole-N-oxide収率 745.9%

試薬・触媒・溶媒 2

HCID 2631-Butanol溶媒HCID 962Water溶媒2 回

反応条件

温度
65 °C

実験手順

2-nitro-4-chloro-2'-hydroxy-3'-t-butyl-5'-methylazobenzene 23.2 g was added to a mixture of n-butanol 60 g, water 10.6 g and 97% sodium hydroxide 6.9 g, and the resultant mixture was stirred while raising temperature to 65° C. Thereafter, the mixture was cooled to 50° C., and 9-fluorenone 1.5 g was added to the mixture. The reaction mixture was then heated to 90° C. in one hour, and the mixture was stirred at 90°~96° C. for five hours to effect reaction, thus almost all of the azobenzene having disappeared. Thereafter, water 50 ml was added to the reaction liquor, and the reaction liquor was neutralized to pH 8~9 with 62% sulfuric acid 10 g to precipitate a crystal. The crystal thus obtained was filtered to separate the crystal, and the separated crystal was then fully washed with water and further with a small amount of methanol. The washed crystal was then dried, thus producing 20.6 g of 2-(2-hydroxy-3-t-butyl-5-methylphenyl)-5-chlorobenzotriazole-N-oxide having a melting point of 160° to 163° C. at the yield of 93.0%.

後処理

  1. temperatureThereafter, the mixture was cooled to 50° C.
  2. temperatureThe reaction mixture was then heated to 90° C. in one hour
  3. customreaction
  4. customto precipitate a crystal
  5. customThe crystal thus obtained
  6. filtrationwas filtered
  7. customto separate the crystal
  8. washthe separated crystal was then fully washed with water and further with a small amount of methanol
  9. customThe washed crystal was then dried

出典と根拠

ORDレコード
ord-eae97202b9914dd7b1d4b40082fa7b76
出典データセット
uspto-grants-1990_07
特許番号
US04943637

関連ノート

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