Propionic Acid → 3-{[4-(3,5-Dinitro-thiophen-2-ylazo)-phenyl]-ethyl-amino}-propionic acid vinyl ester

HRID 252891

반응식

HRID 252891 반응식
[NH2:1][C:2]1[S:3][C:4]([N+:10]([O-:12])=[O:11])=[CH:5][C:6]=1[N+:7]([O-:9])=[O:8].C(O)(=O)CC.N(OS(=O)(=O)O)=O.[CH:25]([O:27][C:28](=[O:40])[CH2:29][CH2:30][N:31]([CH2:38][CH3:39])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)=[CH2:26].S(=O)(=O)(O)[NH2:42]>CO.C(O)(=O)C>[CH:25]([O:27][C:28](=[O:40])[CH2:29][CH2:30][N:31]([C:32]1[CH:37]=[CH:36][C:35]([N:42]=[N:1][C:2]2[S:3][C:4]([N+:10]([O-:12])=[O:11])=[CH:5][C:6]=2[N+:7]([O-:9])=[O:8])=[CH:34][CH:33]=1)[CH2:38][CH3:39])=[CH2:26]

참가 물질

8

반응물 5

HCID 1032Propionic AcidHCID 5987Sulfamic AcidHCID 748952-Thiophenamine, 3,5-dinitro-HCID 82157Nitrosylsulfuric acidHCID 672669143-(Ethyl-phenyl-amino)-propionic acid vinyl ester

생성물 1

HCID 591415123-{[4-(3,5-Dinitro-thiophen-2-ylazo)-phenyl]-ethyl-amino}-propionic acid vinyl ester

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 887Methanol용매

반응 조건

온도
2 °C

실험 절차

5.7 parts of 2-amino-3,5-dinitrothiophene, 20 parts of propionic acid and 30 parts of acetic acid were charged and cooled to 2° C. 11.4 parts of 40% (w/w) nitrosyl sulfuric acid were added, whilst the temperature was held below 4° C. The diazotization mixture was stirred for a further 2 hrs at 2-4° 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 subsequently with water, methanol and again water, then dried to yield 7.4 parts of 3-{[4-(3,5-dinitro-thiophen-2-ylazo)-phenyl]-ethyl-amino}-propionic acid vinyl ester. λmax=626 nm (acetone).

후처리

  1. customwas held below 4° 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

출처 및 근거

ORD 기록
ord-46b1a9e45c8d4f31afae2e44ce4de637
출처 데이터셋
uspto-grants-2011_01
특허 번호
US07871446B2

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