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Hydrochloric Acid → HCID 13881294, Verbindung

HRID 231579
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 231579
Cl[S:2]([C:5]1[CH:14]=[CH:13][CH:12]=[C:11]([N+:15]([O-:17])=[O:16])[C:6]=1[C:7]([O:9][CH3:10])=[O:8])(=[O:4])=[O:3].[NH2:18][CH2:19][CH2:20][CH2:21][OH:22].Cl>C1COCC1>[OH:22][CH2:21][CH2:20][CH2:19][NH:18][S:2]([C:5]1[CH:14]=[CH:13][CH:12]=[C:11]([N+:15]([O-:17])=[O:16])[C:6]=1[C:7]([O:9][CH3:10])=[O:8])(=[O:4])=[O:3]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 90863-Amino-1-propanolHCID 13670189Methyl 2-(chlorosulfonyl)-6-nitrobenzoate

Produkt 1

HCID 13881294HCID 13881294, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of methyl 2-chlorosulfonyl-6-nitrobenzoate (2.80g, 10 mmol) in 100 ml of THF was cooled to ice temperature and stirred in an ice-bath while a solution of 3-amino-1-propanol (99%) (1.67g, 22 mmol) was added dropwise over a period of 45 minutes. Stirring in the ice-bath was continued for 30 minutes. The reaction miture than was acidified by addition of 3.0 ml of 1.2N HCl. The THF was evaporated under reduced pressure and the residue taken up in 100 ml of ethyl acetate. After extracting this solution with 4×20 ml of saturated NaCl solution, the ethyl acetate was evaporated and the residue recrystallized from a mixture of ethyl acetate and hexane to give 2.70g (84.9%) of light yellow crystalline product, m.p., 87-88.5°.

Aufarbeitung

  1. additionwas added dropwise over a period of 45 minutes
  2. customThe THF was evaporated under reduced pressure
  3. extractionAfter extracting this solution with 4×20 ml of saturated NaCl solution
  4. customthe ethyl acetate was evaporated
  5. customthe residue recrystallized from a mixture of ethyl acetate and hexane
  6. customto give 2.70g (84.9%) of light yellow crystalline product, m.p., 87-88.5°

Quellen und Nachweise

ORD-Eintrag
ord-395cd1fe17174bf9804b6379f43a918a
Quelldatensatz
uspto-grants-1989_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04847294

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