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Hydrochloric Acid → Diphenylmethyl [4-[3-(4-thiocarbamoylbenzenesulfonylamino)propyl]-2,3-dioxopiperazin-1-yl]acetate

HRID 1859192
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1859192
[SH2:1].[C:2]([C:4]1[CH:9]=[CH:8][C:7]([S:10]([NH:13][CH2:14][CH2:15][CH2:16][N:17]2[CH2:22][CH2:21][N:20]([CH2:23][C:24]([O:26][CH:27]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)=[O:25])[C:19](=[O:40])[C:18]2=[O:41])(=[O:12])=[O:11])=[CH:6][CH:5]=1)#[N:3].C(N(CC)CC)C.Cl>O.C(OCC)(=O)C.N1C=CC=CC=1>[C:2]([C:4]1[CH:9]=[CH:8][C:7]([S:10]([NH:13][CH2:14][CH2:15][CH2:16][N:17]2[CH2:22][CH2:21][N:20]([CH2:23][C:24]([O:26][CH:27]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=3)=[O:25])[C:19](=[O:40])[C:18]2=[O:41])(=[O:12])=[O:11])=[CH:6][CH:5]=1)(=[S:1])[NH2:3]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 4

HCID 313Hydrochloric AcidHCID 402Hydrogen SulfideHCID 8471TriethylamineHCID 54344221Diphenylmethyl [4-[3-(4-cyanobenzenesulfonylamino)propyl]-2,3-dioxopiperazin-1-yl]acetate

Produkt 1

HCID 54290528Diphenylmethyl [4-[3-(4-thiocarbamoylbenzenesulfonylamino)propyl]-2,3-dioxopiperazin-1-yl]acetate

Reagenzien, Katalysatoren, Lösungsmittel

3
HCID 962WaterLösungsmittelHCID 1049PyridineLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Hydrogen sulfide gas was introduced into a mixture of 0.48 g of diphenylmethyl [4-[3-(4-cyanobenzenesulfonylamino)propyl]-2,3-dioxopiperazin-1-yl]-acetate, 2.4 ml of triethylamine and 4.8 ml of pyridine at room temperature until the mixture was saturated therewith. After stirring at the same temperature for 5 hours, the reaction mixture was added to a mixed solvent of 30 ml of ethyl acetate and 30 ml of water, and the pH was adjusted to 4 with 6N hydrochloric acid. The organic layer was separated and the aqueous layer was re-extracted with 10 ml of ethyl acetate. The combined organic layer was washed with water and then a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and then distilled under reduced pressure to remove the solvent. The resulting residue was purified by a silica gel column chromatography (eluent; chloroform:methanol=20:1) to obtain 0.40 g of diphenylmethyl [4-[3-(4-thiocarbamoylbenzenesulfonylamino)propyl]-2,3-dioxopiperazin-1-yl]acetate as yellow crystals.

Aufarbeitung

  1. customThe organic layer was separated
  2. extractionthe aqueous layer was re-extracted with 10 ml of ethyl acetate
  3. washThe combined organic layer was washed with water
  4. dry with materiala saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate
  5. distillationdistilled under reduced pressure
  6. customto remove the solvent
  7. customThe resulting residue was purified by a silica gel column chromatography (eluent; chloroform:methanol=20:1)

Quellen und Nachweise

ORD-Eintrag
ord-67b24008e4d64dadb083d12a39cc61f6
Quelldatensatz
uspto-grants-2000_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06153613

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