Water → 5-(aminomethyl)-2-chloro-N-cyclopropylbenzenesulfonamide

HRID 1845149Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1845149
[N:1]([CH2:4][C:5]1[CH:6]=[CH:7][C:8]([Cl:18])=[C:9]([S:11]([NH:14][CH:15]2[CH2:17][CH2:16]2)(=[O:13])=[O:12])[CH:10]=1)=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>C1COCC1>[NH2:1][CH2:4][C:5]1[CH:6]=[CH:7][C:8]([Cl:18])=[C:9]([S:11]([NH:14][CH:15]2[CH2:17][CH2:16]2)(=[O:13])=[O:12])[CH:10]=1

Komponenten

5

Edukt 3

HCID 962WaterHCID 11776TriphenylphosphineHCID 866521075-(azidomethyl)-2-chloro-N-cyclopropylbenzenesulfonamide

Produkt 1

HCID 657697715-(aminomethyl)-2-chloro-N-cyclopropylbenzenesulfonamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A round bottom flask was charged with 5-(azidomethyl)-2-chloro-N-cyclopropylbenzenesulfonamide (1.40 g, 4.87 mmol), THF (40 mL), triphenylphosphine (1.6 g, 6.43 mmol) and water (0.11 mL, 6.43 mmol) at 0° C. and the reaction was stirred at room temperature over night. The solvents were removed and the residue was dissolved in MTBE and 20% HCl in dioxane was added dropwise at 0° C. The resulting salt was collected and washed with EtOAc. The salt was then neutralized with 6N NaOH and extracted with CH2Cl2. The combined organic phases were concentrated under reduced pressure to get the title product as a very thick oil. 1H NMR (400 MHz, DMSO-d6): 8.00 (s, 1H), 7.58 (s, 2H), 3.78 (s, 2H), 2.18 (m, 1H), 0.50-0.35 (m, 4H).

Aufarbeitung

  1. customThe solvents were removed
  2. dissolutionthe residue was dissolved in MTBE
  3. addition20% HCl in dioxane was added dropwise at 0° C
  4. customThe resulting salt was collected
  5. washwashed with EtOAc
  6. extractionextracted with CH2Cl2
  7. concentrationThe combined organic phases were concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-0dd6ae224f0a451cae45a6181f20af8e
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08946439B2

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