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

HRID 252891
Notes
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Reaction equation

HRID 252891 reaction equation
[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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 5

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

Product 1

HCID 59141512
3-{[4-(3,5-Dinitro-thiophen-2-ylazo)-phenyl]-ethyl-amino}-propionic acid vinyl ester

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent

Conditions

Temperature
2 °C

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-46b1a9e45c8d4f31afae2e44ce4de637
Source dataset
uspto-grants-2011_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07871446B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes