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

HRID 2166257

반응식

HRID 2166257 반응식
[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

참가 물질

8

반응물 5

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

생성물 1

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

시약·촉매·용매 2

HCID 2631-Butanol용매HCID 962Water용매2회

반응 조건

온도
65 °C

실험 절차

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%.

후처리

  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

출처 및 근거

ORD 기록
ord-eae97202b9914dd7b1d4b40082fa7b76
출처 데이터셋
uspto-grants-1990_07
특허 번호
US04943637

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