Sodium hydride → N-{{2,3-Dibromo-5-(p-chlorophenyl)-4-[(trifluoromethyl)sulfonyl]pyrrol-1-yl}methyl}acetamide

HRID 375180Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 375180
[H-].[Na+].[Br:3][C:4]1[NH:5][C:6]([C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=2)=[C:7]([S:10]([C:13]([F:16])([F:15])[F:14])(=[O:12])=[O:11])[C:8]=1[Br:9].C(O)(=O)C.O[CH2:29][NH:30][C:31](=[O:33])[CH3:32]>O1CCCC1>[Br:3][C:4]1[N:5]([CH2:29][NH:30][C:31](=[O:33])[CH3:32])[C:6]([C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=2)=[C:7]([S:10]([C:13]([F:16])([F:15])[F:14])(=[O:12])=[O:11])[C:8]=1[Br:9]

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 152784202,3-Dibromo-5-(p-chlorophenyl)-4-[(trifluoromethyl)sulfonyl]pyrroleHCID 86745977N-(hydroxymethyl)acetamide acetate

Produkt 1

HCID 15278421N-{{2,3-Dibromo-5-(p-chlorophenyl)-4-[(trifluoromethyl)sulfonyl]pyrrol-1-yl}methyl}acetamideAusbeute 84,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

A mixture of sodium hydride (0.5 g, 60%, 0.0125 mol) and tetrahydrofuran is treated with 2,3-dibromo-5-(p-chlorophenyl)-4-[(trifluoromethyl)sulfonyl]pyrrole (4.67 g, 0.01 mol), stirred for 15 minutes and treated with a solution of N-(hydroxymethyl)acetamide acetate (ester) (1.64 g, 0.0125 mol) in tetrahydrofuran. The reaction mixture is heated at reflux for 18 hours, concentrated in vacuo and poured into a water/ether mixture. The organic phase is separated, washed with water and brine, dried over anhydrous sodium sulfate and concentrated in vacuo to obtain the title product as a white solid (4.56 g).

Aufarbeitung

  1. temperatureThe reaction mixture is heated
  2. temperatureat reflux for 18 hours
  3. concentrationconcentrated in vacuo
  4. additionpoured into a water/ether mixture
  5. customThe organic phase is separated
  6. washwashed with water and brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-dc7f56675ea945a58e64b2354dc6a1d3
Quelldatensatz
uspto-grants-1996_01
Patentnummer
US05484807

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