Propionic Acid → 3-{[4-(2-Chloro-4-nitrophenylazo)-phenyl]-ethyl-amino}-propionic acid vinyl ester

HRID 252889

反応式

HRID 252889 の反応式
[Cl:1][C:2]1[CH:8]=[C:7]([N+:9]([O-:11])=[O:10])[CH:6]=[CH:5][C:3]=1[NH2:4].C(O)(=O)CC.N(OS(=O)(=O)O)=O.[CH:24]([O:26][C:27](=[O:39])[CH2:28][CH2:29][N:30]([CH2:37][CH3:38])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)=[CH2:25].S(=O)(=O)(O)[NH2:41]>CO.C(O)(=O)C>[CH:24]([O:26][C:27](=[O:39])[CH2:28][CH2:29][N:30]([C:31]1[CH:36]=[CH:35][C:34]([N:41]=[N:4][C:3]2[CH:5]=[CH:6][C:7]([N+:9]([O-:11])=[O:10])=[CH:8][C:2]=2[Cl:1])=[CH:33][CH:32]=1)[CH2:37][CH3:38])=[CH2:25]

参加物

8

反応物 5

HCID 1032Propionic AcidHCID 5987Sulfamic AcidHCID 84922-Chloro-4-nitroanilineHCID 82157Nitrosylsulfuric acidHCID 672669143-(Ethyl-phenyl-amino)-propionic acid vinyl ester

生成物 1

HCID 591415103-{[4-(2-Chloro-4-nitrophenylazo)-phenyl]-ethyl-amino}-propionic acid vinyl ester

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒HCID 887Methanol溶媒

反応条件

温度
5 °C

実験手順

5.2 parts of 2-chloro-4-nitroaniline, 20 parts of propionic acid and 30 parts of acetic acid were charged and cooled to 5° C. 11.4 parts of 40% (w/w) nitrosyl sulfuric acid were added, whilst the temperature was held below 10° C. The diazotization mixture was stirred for a further 2 hrs at 5-10° C. To a separate vessel were charged 6.5 parts of 3-(ethyl-phenyl-amino)-propionic acid vinyl ester, 100 parts of methanol, 1 part sulfamic acid and 100 parts of ice. With stirring, the diazotization mixture was slowly added followed by a further 300 parts of ice. The reaction mixture was stirred over night and the product was isolated by filtration, washed with water and dried to yield 9.9 parts of 3-{[4-(2-chloro-4-nitrophenylazo)-phenyl]-ethyl-amino}-propionic acid vinyl ester. λmax=510 nm (DMF).

後処理

  1. customwas held below 10° C
  2. stirringWith stirring
  3. additionthe diazotization mixture was slowly added
  4. stirringThe reaction mixture was stirred over night
  5. customthe product was isolated by filtration
  6. washwashed with water
  7. customdried

出典と根拠

ORDレコード
ord-8cd0f8752a0d4b329b490afb81d525b9
出典データセット
uspto-grants-2011_01
特許番号
US07871446B2

関連ノート

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