Ammonia → Suprofen

HRID 461730ノート

反応式

HRID 461730 の反応式
N.[Na].[C:3]1([C:8]([C:10]2[CH:15]=[CH:14][C:13]([CH2:16][C:17]([OH:19])=[O:18])=[CH:12][CH:11]=2)=[O:9])[S:7][CH:6]=[CH:5][CH:4]=1.[CH3:20]I>C(OCC)C>[C:3]1([C:8]([C:10]2[CH:15]=[CH:14][C:13]([CH:16]([CH3:20])[C:17]([OH:19])=[O:18])=[CH:12][CH:11]=2)=[O:9])[S:7][CH:6]=[CH:5][CH:4]=1

参加物

6

反応物 4

HCID 222AmmoniaHCID 6328Methyl iodideHCID 5360545SodiumHCID 122329832-[p-(2-Thenoyl)phenyl]acetic acid

生成物 1

HCID 5359Suprofen

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

実験手順

To 400 parts of liquid ammonia are added a trace of ferric chloride and 3 parts of sodium. The mixture is stirred for 30 minutes, after which 14.8 parts of 2-[p-(2-thenoyl)phenyl]acetic acid are added slowly during 30 minutes, and the mixture is further stirred for 45 minutes. 13.6 Parts of methyl iodide are added dropwise and the reaction mixture is stirred for 2h. 30 400 parts of diethyl ether are then added and the mixture is stirred overnight. The ammonia is evaporated and the resulting solution is acidified with diluted hydrochloric acid. The ethereal layer is separated and extracted with 10% sodium hydroxide solution. The extract is washed with ether, acidified and extracted with ether. The ethereal solution is dried on sodium sulfate and the ether is evaporated in vacuo. The residue is triturated in petroleumether, filtered off and crystallized twice from acetonitrile, first at -20° C, yielding p-(2-thenoyl)hydratropic acid.

後処理

  1. stirringthe mixture is further stirred for 45 minutes
  2. stirringthe reaction mixture is stirred for 2h
  3. stirringthe mixture is stirred overnight
  4. customThe ammonia is evaporated
  5. customThe ethereal layer is separated
  6. extractionextracted with 10% sodium hydroxide solution
  7. washThe extract is washed with ether
  8. extractionextracted with ether
  9. customThe ethereal solution is dried on sodium sulfate
  10. customthe ether is evaporated in vacuo
  11. customThe residue is triturated in petroleumether
  12. filtrationfiltered off
  13. customcrystallized twice from acetonitrile, first at -20° C

出典と根拠

ORDレコード
ord-eb8aef014bc04dc2b49543fff3015bff
出典データセット
uspto-grants-1977_12
特許番号
US04064132

反応ノート

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