Pyridine → 3,5-Dibromo-2',4-dihydroxybenzanilide

HRID 372493ノート

反応式

HRID 372493 の反応式
[Br:1][C:2]1[CH:7]=[C:6](N)[CH:5]=[C:4]([Br:9])[C:3]=1[OH:10].[N:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[C:17](OC1C(=CC=CC=1)C(Cl)=O)(=[O:19])C.[C:30](OC1C(=CC=CC=1)C(O)=O)(=[O:32])C>CC(C)=O.C(OCC)(=O)C>[Br:1][C:2]1[CH:7]=[C:6]([CH:5]=[C:4]([Br:9])[C:3]=1[OH:10])[C:17]([NH:11][C:16]1[CH:15]=[CH:14][CH:13]=[CH:12][C:30]=1[OH:32])=[O:19]

参加物

7

反応物 4

HCID 1049PyridineHCID 2244AspirinHCID 691074-Amino-2,6-dibromophenolHCID 796682-Acetoxybenzoyl chloride

生成物 1

HCID 203275463,5-Dibromo-2',4-dihydroxybenzanilide収率 78%

試薬・触媒・溶媒 2

HCID 180Acetone溶媒2 回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 was added pyridine (0.32 ml.). Then dropwise and with stirring the solution was added to an acetone solution (10 ml.) containing acetylsalicyloyl chloride which was prepared from acetylsalicylic acid (0.38 g.). Then the reactant 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 ethyl acetate. The residues were 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 compound melts at 182°-187° C.

後処理

  1. customThen the reactant solution was evaporated to dryness under reduced pressure
  2. customto give a residue which
  3. washAfter washing first with water
  4. customwith 1 N hydrochloric acid, the solution was evaporated under reduced pressure
  5. customto remove ethyl acetate
  6. dissolutionThe residues were redissolved in a mixture of methanol and 2 N sodium hydroxide (10 ml
  7. stirringStirring this solution for several hours
  8. customprecipitated the product which
  9. customwas recrystallized from aqueous methanol

出典と根拠

ORDレコード
ord-a66b73c170ac42cf97d37182acfca647
出典データセット
uspto-grants-1978_05
特許番号
US04091097

反応ノート

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