Aspirin → Benzamide, N-(3,5-dibromo-4-hydroxyphenyl)-2-hydroxy-

HRID 437933

反応式

HRID 437933 の反応式
[Br:1][C:2]1[CH:7]=[C:6]([NH2:8])[CH:5]=[C:4]([Br:9])[C:3]=1[OH:10].C([O:14][C:15]1[C:16](=[CH:20][CH:21]=[CH:22][CH:23]=1)[C:17](Cl)=[O:18])(=O)C.C(OC1C(=CC=CC=1)C(O)=O)(=O)C>CC(C)=O.N1C=CC=CC=1.C(OCC)(=O)C>[Br:1][C:2]1[CH:7]=[C:6]([CH:5]=[C:4]([Br:9])[C:3]=1[OH:10])[NH:8][C:17](=[O:18])[C:16]1[CH:20]=[CH:21][CH:22]=[CH:23][C:15]=1[OH:14]

参加物

7

反応物 3

HCID 2244AspirinHCID 691074-Amino-2,6-dibromophenolHCID 796682-Acetoxybenzoyl chloride

生成物 1

HCID 3043338Benzamide, N-(3,5-dibromo-4-hydroxyphenyl)-2-hydroxy-収率 78%

試薬・触媒・溶媒 3

HCID 180Acetone溶媒2 回HCID 1049Pyridine溶媒HCID 8857Ethyl Acetate溶媒

実験手順

2,6-Dibromo-4-aminophenol (0.6 g.) was dissolved in acetone (30 ml.) to which pyridine (0.32 ml.) was added. Then the solution was added by drops and with stirring to an acetone solution (10 ml.) containing acetylsalicyloyl chloride which was prepared from acetyl-salicylic acid (0.38 g.). The resulting solution was evaporated to dryness under reduced pressure to give a residue which was dissolved in ethyl acetate. After washing first with water and then with 1 N hydrochloric acid the solution was evaporated under reduced pressure to remove the ethyl acetate. The residue was redissolved in a mixture of methanol and 2 N sodium hydroxide (10 ml. each). Stirring this solution for several hours and acidifying with 2 N hydrochloric acid precipitated the product which was recrystallized from aqueous methanol to give light brown crystals of 3',5'-dibromo-2,4'-dihydroxybenzanilide (0.88 g.). Yield: 78%. The melting point of the compound is 182°-187° C.

後処理

  1. additionwas added
  2. additionThen the solution was added by drops
  3. customThe resulting solution was evaporated to dryness under reduced pressure
  4. customto give a residue which
  5. washAfter washing first with water
  6. customwith 1 N hydrochloric acid the solution was evaporated under reduced pressure
  7. customto remove the ethyl acetate
  8. dissolutionThe residue was redissolved in a mixture of methanol and 2 N sodium hydroxide (10 ml
  9. customprecipitated the product which
  10. customwas recrystallized from aqueous methanol

出典と根拠

ORDレコード
ord-b1aaf3b3614749d6bd969b2015b3de0c
出典データセット
uspto-grants-1977_06
特許番号
US04032635

関連ノート

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