Potassium Iodide → 5-Chloro-2-propoxybenzamide

HRID 1460978

反応式

HRID 1460978 の反応式
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([OH:11])=[C:6]([CH:10]=1)[C:7]([NH2:9])=[O:8].Br[CH2:13][CH2:14][CH3:15].[I-].[K+].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:11][CH2:13][CH2:14][CH3:15])=[C:6]([CH:10]=1)[C:7]([NH2:9])=[O:8]

参加物

6

反応物 4

HCID 4875Potassium IodideHCID 78401-BromopropaneHCID 11430Potassium CarbonateHCID 3480945-Chloro-2-hydroxybenzamide

生成物 1

HCID 94528845-Chloro-2-propoxybenzamide

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

A stirred mixture of 5-chloro-2-hydroxybenzamide (20 g), 1-bromopropane (13.4 ml), potassium iodide (2.49 g) and anhydrous potassium carbonate (24.15 g) in acetone (250 ml) was heated under reflux for 20 hours. The cooled reaction mixture was filtered and the filter cake was washed with acetone. The filtrate and washings were combined and evaporated under reduced pressure to yield a residue which was washed with water, dilute aqueous sodium hydroxide, water and with diethyl ether to yield a crude product (19.85 g). This was recrystallised from acetonitrile, partitioned between chloroform and dilute aqueous sodium hydroxide, and was recrystallised from ethanol to yield 5-chloro-2-propoxybenzamide (16.78 g).

後処理

  1. temperaturewas heated
  2. temperatureunder reflux for 20 hours
  3. customThe cooled reaction mixture
  4. filtrationwas filtered
  5. washthe filter cake was washed with acetone
  6. customevaporated under reduced pressure
  7. customto yield a residue which
  8. washwas washed with water, dilute aqueous sodium hydroxide, water and with diethyl ether
  9. customto yield a crude product (19.85 g)
  10. customThis was recrystallised from acetonitrile
  11. custompartitioned between chloroform and dilute aqueous sodium hydroxide
  12. customwas recrystallised from ethanol

出典と根拠

ORDレコード
ord-28af009435194eb6bf88e957b6f73117
出典データセット
uspto-grants-1991_12
特許番号
US05073559

関連ノート

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