Hydrochloric Acid → HCID 20429536, Verbindung

HRID 615208Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 615208
[C:1](O)(=O)[CH2:2][CH2:3][CH2:4][C:5]#[C:6][CH2:7][C:8]#[C:9][CH2:10][C:11]#[C:12][CH2:13][C:14]#[C:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]C.S(Cl)(Cl)=[O:25].C[N:29](C)[CH:30]=[O:31].Cl>C(Cl)Cl.CCOCC>[C:30]([NH:29][OH:25])(=[O:31])[CH2:20][CH2:19][CH2:18][C:17]#[C:16][CH2:15][C:14]#[C:13][CH2:12][C:11]#[C:10][CH2:9][C:8]#[C:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1]

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 1522675,8,11,14-Heneicosatetraynoic acid

Produkt 1

HCID 20429536HCID 20429536, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

Heneicosa-5,8,11,14-tetraynoic acid (130 mg) was dissolved in methylene chloride (3 ml) and a solution of thionyl chloride (104 mg) and dimethylformamide (5 mg) in methylene chloride (2.6 ml) was added. After 3 hours at 25° C., the solution was evaporated. To the residue was added a solution of hydroxylamine hydrochloride (58 mg) and sodium bicarbonate (70 mg) in water (0.4 ml) and methanol (0.4 ml) to which had been added normal aqueous potassium hydroxide sufficient to obtain a pH of 9. After 10 minutes ether (20 ml) and 1.0N hydrochloric acid (10 ml) were added. The organic solution was dried and evaporated, and the residue was chromatographed on silica gel, eluting with methylene chloride/methanol/ammonium hydroxide, (40/4/0.3;v/v/v) so as to afford the title compound as a solid, m.p.: 85°-88° C.

Aufarbeitung

  1. customthe solution was evaporated
  2. additionTo the residue was added a solution of hydroxylamine hydrochloride (58 mg) and sodium bicarbonate (70 mg) in water (0.4 ml) and methanol (0.4 ml) to which
  3. additionhad been added normal aqueous potassium hydroxide sufficient
  4. customto obtain a pH of 9
  5. customThe organic solution was dried
  6. customevaporated
  7. customthe residue was chromatographed on silica gel
  8. washeluting with methylene chloride/methanol/ammonium hydroxide, (40/4/0.3;v/v/v) so as

Quellen und Nachweise

ORD-Eintrag
ord-2a839eaf191c47aea14b6d4c833f77a1
Quelldatensatz
uspto-grants-1985_02
Patentnummer
US04497827

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