Hydrochloric Acid → 4'-(3-(1-Pyrrolidinyl)propionyl)methanesulfonanilide hydrochloride

HRID 917995

Reaktionsgleichung

Reaktionsgleichung von HRID 917995
[C:1]([C:4]1[CH:14]=[CH:13][C:7]([NH:8][S:9]([CH3:12])(=[O:11])=[O:10])=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[CH2:15]=O.[ClH:17].[NH:18]1[CH2:22][CH2:21][CH2:20][CH2:19]1.Cl>C(O)C>[ClH:17].[N:18]1([CH2:15][CH2:2][C:1]([C:4]2[CH:14]=[CH:13][C:7]([NH:8][S:9]([CH3:12])(=[O:10])=[O:11])=[CH:6][CH:5]=2)=[O:3])[CH2:22][CH2:21][CH2:20][CH2:19]1

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 212848Pyrrolidine, hydrochloride (1:1)HCID 684083N-(4-acetylphenyl)methanesulfonamide

Produkt 1

HCID 30426934'-(3-(1-Pyrrolidinyl)propionyl)methanesulfonanilide hydrochloride

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of 4'-acetylmethanesulfonanilide (21.5 g., 0.1 mole), 95% paraformaldehyde (10 g., 0.3 mole), pyrrolidine hydrochloride (10.8 g., 0.1 mole) in 150 ml. of ethanol containing 1 drop of concentrated hydrochloric acid is refluxed for a period of 4 hr. at steam bath temperature and then for an additional period of 8 hr. permitting the ethanol to evaporate. The resulting glassy residue is stirred with 300 ml. of hot acetone providing a crystalline material which is collected and crystallized from methanol-isopropyl alcohol to afford analytically pure 4'-[3-(1-PYRROLIDINYL)PROPIONYL]-METHANESULFONANILIDE HYDROCHLORIDE, m.p. 182.0°-183.0°C.

Aufarbeitung

  1. customto evaporate
  2. customof hot acetone providing a crystalline material which is collected
  3. customcrystallized from methanol-isopropyl alcohol

Quellen und Nachweise

ORD-Eintrag
ord-e567233c2e9e45eba084244edecee822
Quelldatensatz
uspto-grants-1976_07
Patentnummer
US03968242

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