Ammonium Chloride → Tert-butyl 5-aminothiophene-2-carboxylate

HRID 59747ノート

反応式

HRID 59747 の反応式
[N+:1]([C:4]1[S:8][C:7]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])=[CH:6][CH:5]=1)([O-])=O.[Cl-].[NH4+]>CCO.O.[Fe]>[NH2:1][C:4]1[S:8][C:7]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])=[CH:6][CH:5]=1

参加物

6

反応物 2

HCID 25517Ammonium ChlorideHCID 23344844Tert-butyl 5-nitrothiophene-2-carboxylate

生成物 1

HCID 86703850Tert-butyl 5-aminothiophene-2-carboxylate収率 76.4%

試薬・触媒・溶媒 3

HCID 23925Iron触媒HCID 702Ethanol溶媒HCID 962Water溶媒

反応条件

温度
80 °C

実験手順

To a suspension of tert-butyl 5-nitrothiophene-2-carboxylate (Int. 54) (2.230 g, 9.73 mmol) in a mixture of EtOH (60 ml) and water (30 ml), iron powder (3.26 g, 58.4 mmol) and ammonium chloride (0.364 g, 6.81 mmol) were added. The reaction was stirred at 80° C. for 3 hours and then at RT overnight. The mixture was filtered through a celite pad and the filtrate was evaporated to dryness. The crude was then dissolved in EtOAc and washed with brine; the organic phase was dried over sodium sulfate and the solvent evaporated under vacuum. The residue was purified by filtration through a silica gel cartridge (petroleum ether/EtOAc=9/1 to 6/4) to yield tert-butyl 5-aminothiophene-2-carboxylate (Int. 55) (1.481 g, 7.43 mmol, MS/ESI+200.0 [MH]+).

後処理

  1. additionwere added
  2. customat RT
  3. customovernight
  4. filtrationThe mixture was filtered through a celite pad
  5. customthe filtrate was evaporated to dryness
  6. dissolutionThe crude was then dissolved in EtOAc
  7. washwashed with brine
  8. dry with materialthe organic phase was dried over sodium sulfate
  9. customthe solvent evaporated under vacuum
  10. filtrationThe residue was purified by filtration through a silica gel cartridge (petroleum ether/EtOAc=9/1 to 6/4)

出典と根拠

ORDレコード
ord-0449aa2472d54828938340e2b80d282d
出典データセット
uspto-grants-2016_09
特許番号
US09440954B2

反応ノート

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