Hydrogen Bromide → N-((S)-3-bromo-2-hydroxypropyl)-5-chlorothiophene-2-carboxamide

HRID 425235Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 425235
[BrH:1].[OH:2][C@H:3]([CH2:14]O)[CH2:4][NH:5][C:6]([C:8]1[S:9][C:10]([Cl:13])=[CH:11][CH:12]=1)=[O:7].C(OC(=O)C)(=O)C.CO>C(O)(=O)C>[Br:1][CH2:14][C@@H:3]([OH:2])[CH2:4][NH:5][C:6]([C:8]1[S:9][C:10]([Cl:13])=[CH:11][CH:12]=1)=[O:7]

Komponenten

6

Edukt 4

HCID 260Hydrogen BromideHCID 887MethanolHCID 7918Acetic AnhydrideHCID 99916905-Chloro-N-((S)-2,3-dihydroxypropyl)thiophene-2-carboxamide

Produkt 1

HCID 10108741N-((S)-3-bromo-2-hydroxypropyl)-5-chlorothiophene-2-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel2×

Reaktionsbedingungen

Temperatur
62.5 °C

Versuchsvorschrift

301.7 ml of a 33% solution of hydrobromic acid in acetic acid are added to a suspension of 100 g of N-((S)-2,3-dihydroxypropyl)-5-chlorothiophene-2-carboxamide (VIII) in 250 ml of glacial acetic acid at from 21 to 26° C. over a period of 30 minutes. Subsequently, 40 ml of acetic anhydride are added and the reaction mixture is stirred at from 60 to 65° C. for three hours. At 20 to 25° C., 960 ml of methanol are then added over a period of 30 minutes. The reaction mixture is stirred under reflux for 2.5 hours and then overnight at from 20 to 25° C. For workup, the solvents are distilled off under reduced pressure at approx. 95 mbar. The remaining suspension is admixed with 50 ml of 1-butanol and 350 ml of water. The precipitated product is filtered off with suction, washed with water and dried.

Aufarbeitung

  1. stirringThe reaction mixture is stirred
  2. temperatureunder reflux for 2.5 hours
  3. customovernight
  4. customat from 20 to 25° C
  5. distillationFor workup, the solvents are distilled off under reduced pressure at approx. 95 mbar
  6. filtrationThe precipitated product is filtered off with suction
  7. washwashed with water
  8. customdried

Quellen und Nachweise

ORD-Eintrag
ord-2cc01475d2b741888dc6133267712869
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08106192B2

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