1,1'-Carbonyldiimidazole → N-(3-methoxy-benzyl)-N-methyl-2-(3,5-dimetoxyphenyl)-2-(phenylsulfanyl)-acetamide

HRID 1666308

Reaktionsgleichung

Reaktionsgleichung von HRID 1666308
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]([S:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:12]([OH:14])=O)[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.[CH3:34][NH:35][CH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[C:39]([O:43][CH3:44])[CH:38]=1>ClCCl>[CH3:44][O:43][C:39]1[CH:38]=[C:37]([CH:42]=[CH:41][CH:40]=1)[CH2:36][N:35]([CH3:34])[C:12](=[O:14])[CH:11]([C:5]1[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=[C:3]([O:2][CH3:1])[CH:4]=1)[S:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Komponenten

5

Edukt 3

HCID 682631,1'-CarbonyldiimidazoleHCID 51522253-Methoxy-N-methylbenzylamineHCID 670817982-(3,5-Dimethoxyphenyl)-2-(phenylsulfanyl)acetic acid

Produkt 1

HCID 67081986N-(3-methoxy-benzyl)-N-methyl-2-(3,5-dimetoxyphenyl)-2-(phenylsulfanyl)-acetamideAusbeute 105,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

A solution of 2-(3,5-dimethoxyphenyl)-2-(phenyl-sulfanyl)acetic acid (6.0 g) in dichloromethane (50 ml) was treated with 1,1′-carbonyldiimidazole (3.24 g) at room temperature for 2 hours. A solution of N-methyl-3-methoxy-benzylamine (3.4 g) in dichloromethane (15 ml) was added and the stirring was continued for one hour. The reaction mixture was washed with aqueous hydrochloric acid (1M, 50 ml) and aqueous sodium hydroxide (1M, 50 ml). The organic phase was dried and concentrated to dryness leaving crude N-(3-methoxy-benzyl)-N-methyl-2-(3,5-dimetoxyphenyl)-2-(phenylsulfanyl)-acetamide (9.1 g) as a viscous oil.

Aufarbeitung

  1. washThe reaction mixture was washed with aqueous hydrochloric acid (1M, 50 ml) and aqueous sodium hydroxide (1M, 50 ml)
  2. customThe organic phase was dried
  3. concentrationconcentrated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-370fd67e1c1a41fba3ad8e657cd42e69
Quelldatensatz
uspto-grants-2011_10
Patentnummer
US08044067B2

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