Acetic Acid → Benzenamine, 4-chloro-N-ethyl-2-nitro-

HRID 1734548

反応式

HRID 1734548 の反応式
[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1.[CH:12](=O)[CH3:13].CC(O)=O.C(O)(C(F)(F)F)=O>C1(C)C=CC=CC=1.N1C=CC=CC=1.CCOC(C)=O.CCCCCC>[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][CH2:12][CH3:13])=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1

参加物

8

反応物 4

HCID 176Acetic AcidHCID 177Acetaldehyde2 回HCID 6422Trifluoroacetic acidHCID 69794-Chloro-2-nitroaniline2 回

生成物 1

HCID 97006Benzenamine, 4-chloro-N-ethyl-2-nitro-収率 50%

試薬・触媒・溶媒 3

HCID 1049Pyridine溶媒2 回HCID 1140Toluene溶媒HCID 21226206Ethyl acetate hexane溶媒

実験手順

4-chloro-2-nitroaniline (8.6 g; 0.05 mole), acetaldehyde (5.5 ml; 0.05 mole) and HOAc (4.0 ml; 0.1 moles) were dissolved in toluene (100 ml) and stirred for 1 hr. BH3 * pyridine (5.0 ml; 0.01 moles) was added in 1.0 ml increments. The reaction was exothermic, and the reaction progress was monitored by tlc (40% EtOAc/Hexane). Additional TFA, BH3 * pyridine and acetaldehyde were added until the tlc indicated that the 4-chloro-2-nitroaniline was consumed. The reaction mixture was washed 2× with water and placed on a bed of silica and eluted with 20% EtOAc/Hexane. The product was the first major component to elute. The product was crystallized from MeOH which produced 5.0 g (50%) of a yellow crystalline solid.

後処理

  1. customwas consumed
  2. washThe reaction mixture was washed 2× with water
  3. washeluted with 20% EtOAc/Hexane
  4. washto elute
  5. customThe product was crystallized from MeOH which

出典と根拠

ORDレコード
ord-b0d2e24a3ce64d18b6543d48c6401165
出典データセット
uspto-grants-1996_07
特許番号
US05534521

関連ノート

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