Pyrrolidine → 4-(Pyrrolidine-1-sulfonyl)benzoic acid

HRID 72974

Reaktionsgleichung

Reaktionsgleichung von HRID 72974
Cl[S:2]([C:5]1[CH:13]=[CH:12][C:8]([C:9]([OH:11])=[O:10])=[CH:7][CH:6]=1)(=[O:4])=[O:3].[NH:14]1[CH2:18][CH2:17][CH2:16][CH2:15]1>ClCCl>[N:14]1([S:2]([C:5]2[CH:13]=[CH:12][C:8]([C:9]([OH:11])=[O:10])=[CH:7][CH:6]=2)(=[O:4])=[O:3])[CH2:18][CH2:17][CH2:16][CH2:15]1

Komponenten

4

Edukt 2

HCID 31268PyrrolidineHCID 823854-(Chlorosulfonyl)benzoic acid

Produkt 1

HCID 7636514-(Pyrrolidine-1-sulfonyl)benzoic acidAusbeute 30,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a solution of 4-chlorosulfonylbenzoic acid (2 g, 9.07 mmol) in dichloromethane (10 mL) was added a solution of pyrrolidine (1.29 g, 1.51 mL, 18.1 mmol) in dichloromethane (10 mL) and the reaction mixture was stirred at room temperature for 24 hours. The reaction mixture was filtered and the white solid obtained was washed with water (50 ml) and diethyl ether (10 ml) and dried under vacuum to give 4-pyrrolidin-1-ylsulfonylbenzoic acid (700 mg, 30%). ESI-MS m/z calc. 255.0. Found 256.3 (M+1)+; Retention time: 1.18 minutes (3 min run); 1H NMR (400 MHz, DMSO) δ 13.49 (s, 1H), 8.15 (d, J=8.5 Hz, 2H), 7.92 (d, J=8.5 Hz, 2H), 3.17 (t, J=6.7 Hz, 4H), 1.65 (t, J=6.7 Hz, 4H).

Aufarbeitung

  1. filtrationThe reaction mixture was filtered
  2. customthe white solid obtained
  3. washwas washed with water (50 ml) and diethyl ether (10 ml)
  4. customdried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-0485f254a93b4844907c5f29d2a44550
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08828996B2

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