Triethylamine hydrochloride → HCID 178421874, Verbindung

HRID 1489186Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1489186
[C:1]([C:3]1[CH:15]=[CH:14][C:6]2[O:7][C:8]([CH3:13])([CH3:12])[C:9]([CH3:11])=[CH:10][C:5]=2[CH:4]=1)#[N:2].[N-:16]=[N+:17]=[N-:18].[Na+].Cl.C(N(CC)CC)C.[OH-].[Na+]>O.CN1CCCC1=O>[NH:16]1[C:1]([C:3]2[CH:15]=[CH:14][C:6]3[O:7][C:8]([CH3:12])([CH3:13])[C:9]([CH3:11])=[CH:10][C:5]=3[CH:4]=2)=[N:2][N:18]=[N:17]1

Komponenten

7

Edukt 4

HCID 11130Triethylamine hydrochlorideHCID 14798Sodium HydroxideHCID 33557Sodium AzideHCID 145179846-cyano-2,2,3-trimethyl-2H-benzo[b]pyran

Produkt 1

HCID 178421874HCID 178421874, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Reaktionsbedingungen

Temperatur
150 °C

Versuchsvorschrift

A mixture of 6-cyano-2,2,3-trimethyl-2H-benzo[b]pyran (see J. Med. Chem., 1991, 34, 3074) (4 g), sodium azide (4.0 g), triethylamine hydrochloride (4.2 g) and 1-methyl-2-pyrrolidinone (40 ml), was heated at 150° C. for 1 hour. On cooling to room temperature water (200 ml) was added and the mixture was brought to pH 14 by the addition of solid sodium hydroxide. The solution was extracted with ethyl acetate (200 ml) then acidified to pH 3-4 with concentrated hydrochloric acid to give a solid which was filtered off, washed with water and dried to give the title compound, 4.5 g, m.p. 179°-181° C. Found: C, 64.58; H, 5.81; N, 23.46; C13H14N4O requires: C, 64.45; H, 5.82; N, 23.13%.

Aufarbeitung

  1. additionwas added
  2. extractionThe solution was extracted with ethyl acetate (200 ml)
  3. customto give a solid which
  4. filtrationwas filtered off
  5. washwashed with water
  6. customdried

Quellen und Nachweise

ORD-Eintrag
ord-6950270ca111401ca922a81e2ab12fa7
Quelldatensatz
uspto-grants-1997_10
Patentnummer
US05677324

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