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2-Aminophenol → 4-bromo-N-(2-hydroxyphenyl)benzamide

HRID 1502560
ノート
印刷プレビュー

反応式

HRID 1502560 の反応式
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8].C(N(CC)CC)C.O1CCCC1.[Br:21][C:22]1[CH:30]=[CH:29][C:25]([C:26](Cl)=[O:27])=[CH:24][CH:23]=1>O>[Br:21][C:22]1[CH:30]=[CH:29][C:25]([C:26]([NH:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[OH:8])=[O:27])=[CH:24][CH:23]=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 58012-AminophenolHCID 8028Tetrahydrofuran2 回HCID 8471TriethylamineHCID 685154-Bromobenzoyl chloride

生成物 1

HCID 8310534-bromo-N-(2-hydroxyphenyl)benzamide

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
0 °C

実験手順

In a 200 mL three-necked flask were placed 2.2 g (20 mmol) of 2-aminophenol, 3.0 mL (22 mmol) of triethylamine, and 50 mL of tetrahydrofuran (THF). Then, the mixture was cooled to 0° C. After cooling, 50 mL of a THF solution containing 4.5 g (20 mmol) of 4-bromobenzoyl chloride was dripped under a nitrogen stream. This solution was stirred at 0° C. for 4 hours under a nitrogen stream. After a certain time, water was added to the solution, and an aqueous layer was extracted with ethyl acetate. The resulting extract was combined with the organic layer, and the organic layer was washed with 0.2 M hydrochloric acid and a saturated aqueous solution of sodium bicarbonate, and then dried with magnesium sulfate. The mixture was subjected to suction filtration through Celite (produced by Wako Pure Chemical Industries, Ltd., Catalog No. 531-16855), and the filtrate was condensed to give a solid. The obtained solid was recrystallized with ethyl acetate/hexane, so that 5.3 g of target white powder was obtained in a yield of 88%.

後処理

  1. customIn a 200 mL three-necked flask were placed
  2. temperatureAfter cooling
  3. extractionan aqueous layer was extracted with ethyl acetate
  4. extractionThe resulting extract
  5. washthe organic layer was washed with 0.2 M hydrochloric acid
  6. dry with materiala saturated aqueous solution of sodium bicarbonate, and then dried with magnesium sulfate
  7. filtrationThe mixture was subjected to suction filtration through Celite (produced by Wako Pure Chemical Industries, Ltd., Catalog No. 531-16855)
  8. customcondensed
  9. customto give a solid
  10. customThe obtained solid was recrystallized with ethyl acetate/hexane, so that 5.3 g of target white powder
  11. customwas obtained in a yield of 88%

出典と根拠

ORDレコード
ord-eca649fa49294cd980bb0bfcc8c16e27
出典データセット
uspto-grants-2015_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09209408B2

反応ノート

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