Propionic Acid → 3-{Ethyl-[3-methyl-4-(5-nitro-thiazol-2-ylazo)-phenyl]-amino}-propionic acid vinyl ester

HRID 252892

反応式

HRID 252892 の反応式
[NH2:1][C:2]1[S:3][C:4]([N+:7]([O-:9])=[O:8])=[CH:5][N:6]=1.C(O)(=O)CC.N(OS(=O)(=O)O)=O.[CH:22]([O:24][C:25](=[O:38])[CH2:26][CH2:27][N:28]([CH2:36][CH3:37])[C:29]1[CH:34]=[CH:33][CH:32]=[C:31]([CH3:35])[CH:30]=1)=[CH2:23].S(=O)(=O)(O)[NH2:40]>CO.C(O)(=O)C>[CH:22]([O:24][C:25](=[O:38])[CH2:26][CH2:27][N:28]([CH2:36][CH3:37])[C:29]1[CH:34]=[CH:33][C:32]([N:40]=[N:1][C:2]2[S:3][C:4]([N+:7]([O-:9])=[O:8])=[CH:5][N:6]=2)=[C:31]([CH3:35])[CH:30]=1)=[CH2:23]

参加物

8

反応物 5

HCID 1032Propionic AcidHCID 5987Sulfamic AcidHCID 84862-Amino-5-NitrothiazoleHCID 82157Nitrosylsulfuric acidHCID 672666093-(Ethyl-[3-methylphenyl]-amino)-propionic acid vinyl ester

生成物 1

HCID 591415153-{Ethyl-[3-methyl-4-(5-nitro-thiazol-2-ylazo)-phenyl]-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

4.4 parts of 2-amino-5-nitrothiazole, 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 7.0 parts of 3-(ethyl-[3-methylphenyl]-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 subsequently with water, methanol and again water, then dried to yield 9.5 parts of 3-{ethyl-[3-methyl-4-(5-nitro-thiazol-2-ylazo)-phenyl]-amino}-propionic acid vinyl ester. λmax=602 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 subsequently with water, methanol and again water
  7. customdried

出典と根拠

ORDレコード
ord-35a24bb26dbf4fc9a03ad3f5057ed95c
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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