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Triethylamine → 5-Methoxyacetylamino-2,4,6-triiodoisophthalic acid (2,3-dihydroxypropyl)amide chloride

HRID 1967635
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1967635
[NH2:1][C:2]1[C:3]([I:16])=[C:4]([C:13](Cl)=[O:14])[C:5]([I:12])=[C:6]([C:10]=1[I:11])[C:7]([Cl:9])=[O:8].[CH3:17][O:18][CH2:19][C:20](Cl)=[O:21].C(N(CC)CC)C.[OH:30][CH:31]([CH2:34][OH:35])[CH2:32][NH2:33].CC(N(C)C)=[O:38]>O.C(Cl)Cl>[Cl-:9].[OH:30][CH:31]([CH2:34][OH:35])[CH2:32][NH:33][C:13](=[O:14])[C:4]1[C:3]([I:16])=[C:2]([NH:1][C:20](=[O:21])[CH2:19][O:18][CH3:17])[C:10]([I:11])=[C:6]([C:7]([OH:38])=[O:8])[C:5]=1[I:12]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 5

HCID 8471TriethylamineHCID 31374Dimethylacetamide2×HCID 735613-Amino-1,2-propanediolHCID 96623Methoxyacetyl chlorideHCID 98948585-Amino-2,4,6-triiodoisophthaloyl dichloride

Produkt 1

HCID 86650908
5-Methoxyacetylamino-2,4,6-triiodoisophthalic acid (2,3-dihydroxypropyl)amide chloride

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
15 °C

Versuchsvorschrift

5-amino-2,4,6-triiodoisophthalic acid dichloride (13.7 kg, 23 mol) was dissolved in dimethylacetamide (17.2 kg) and the mixture was cooled to 15° C. Methoxyacetyl chloride (3.74 kg, 34.5 mol) was added dropwise thereto for 2 hours, and then the mixture was stirred for 15 hours. After confirming the disappearance of the starting material by HPLC analysis for reaction, methylene chloride (45.7 kg) and water (11.5 kg) were subsequently added to the reaction mixture upon being stirred, and then the stirring was stopped and the layers became separated. The obtained organic layer was washed with aqueous sodium bicarbonate solution and concentrated by distillation under reduced pressure. To a solution of the obtained concentrate dissolved in dimethylacetamide (43.1 kg), triethylamine (1.95 kg, 19.32 mol) was added and then a solution of 2,3-dihydroxypropylamine (1.47 kg, 16.13 mol) dissolved in dimethylacetamide (10.78 kg) was added dropwise thereto for 5 hours with maintaining 0 to 5° C. After additional 3 hours with stirring, the reaction mixture was concentrated by distillation under reduced pressure and to the concentrate, methylene dichloride (213.33 kg) was added dropwise for 5 hours to form solid. The solid was filtered and the title compound was obtained as a white solid (10.98 kg, yield 66.1%).

Aufarbeitung

  1. additionwere subsequently added to the reaction mixture
  2. stirringupon being stirred
  3. customthe layers became separated
  4. washThe obtained organic layer was washed with aqueous sodium bicarbonate solution
  5. concentrationconcentrated by distillation under reduced pressure
  6. concentrationTo a solution of the obtained concentrate
  7. dissolutiondissolved in dimethylacetamide (43.1 kg)
  8. additionwas added dropwise
  9. temperaturefor 5 hours with maintaining 0 to 5° C
  10. stirringAfter additional 3 hours with stirring
  11. concentrationthe reaction mixture was concentrated by distillation under reduced pressure and to the concentrate, methylene dichloride (213.33 kg)
  12. additionwas added dropwise for 5 hours
  13. customto form solid
  14. filtrationThe solid was filtered

Quellen und Nachweise

ORD-Eintrag
ord-70bc38e9f44b45b5a9db746196d553a9
Quelldatensatz
uspto-grants-2013_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08420858B2

Notizen zur Reaktion

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