Salicylamide → 2-(2-Methylpropoxy)benzamide

HRID 1288264

反応式

HRID 1288264 の反応式
[C:1]([NH2:10])(=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4].[Na].[CH2:12](Br)[CH:13]([CH3:15])[CH3:14]>C(O)C>[CH2:12]([O:4][C:3]1[CH:5]=[CH:6][CH:7]=[CH:8][C:2]=1[C:1]([NH2:10])=[O:9])[CH:13]([CH3:15])[CH3:14]

参加物

5

反応物 3

HCID 5147SalicylamideHCID 65551-Bromo-2-methylpropaneHCID 5360545Sodium

生成物 1

HCID 49464332-(2-Methylpropoxy)benzamide

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

Salicylamide (68.5 g.; prepared as described by R. Bogoczek, Farm. Polska, 1960, 16, 26) was added to a solution of sodium (11.5 g.) in anhydrous ethanol (400 ml.). Isobutyl bromide (60 ml.) was then added, and the mixture was stirred and heated to reflux overnight. The ethanol was evaporated, and sufficient water was added to the residue to dissolve the sodium bromide. The oil which did not dissolve was extracted with chloroform, the extract was washed twice with 2N sodium hydroxide solution and once with water, dried over magnesium sulphate, filtered and evaporated. The residue was triturated with light petroleum (b.p. 40°-60° C.) to give 2-isobutoxybenzamide, which was pure enough for use in the next stage of the synthesis. A pure sample, m.p. 125°-128° C., was obtained by recrystallisation of an aliquot from cyclohexane.

後処理

  1. temperatureheated
  2. temperatureto reflux overnight
  3. customThe ethanol was evaporated
  4. additionsufficient water was added to the residue
  5. dissolutionto dissolve the sodium bromide
  6. dissolutionThe oil which did not dissolve
  7. extractionwas extracted with chloroform
  8. washthe extract was washed twice with 2N sodium hydroxide solution and once with water
  9. dry with materialdried over magnesium sulphate
  10. filtrationfiltered
  11. customevaporated
  12. customThe residue was triturated with light petroleum (b.p. 40°-60° C.)

出典と根拠

ORDレコード
ord-e85522e5c58742ffa7d9f7068f609f70
出典データセット
uspto-grants-1976_10
特許番号
US03987160

関連ノート

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