Ammonia → 6-Bromo-5'-methylspiro[chromane-4,2'-imidazol]-4'-amine

HRID 539264Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 539264
[Br:1][C:2]1[CH:3]=[C:4]2[C:11]3([N:15]=[C:14]([CH3:16])[C:13](=S)[NH:12]3)[CH2:10][CH2:9][O:8][C:5]2=[CH:6][CH:7]=1.[NH3:18]>CO>[Br:1][C:2]1[CH:3]=[C:4]2[C:11]3([N:12]=[C:13]([NH2:18])[C:14]([CH3:16])=[N:15]3)[CH2:10][CH2:9][O:8][C:5]2=[CH:6][CH:7]=1

Komponenten

4

Edukt 2

HCID 222AmmoniaHCID 866672686-Bromo-4'-methylspiro[chromane-4,2'-imidazole]-5'(1'H)-thione2×

Produkt 1

HCID 679796056-Bromo-5'-methylspiro[chromane-4,2'-imidazol]-4'-amineAusbeute 77 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel2×

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

6-Bromo-4′-methylspiro[chroman-4,2′-imidazole]-5′(1′H)-thione (0.10 g, 0.32 mmol, Intermediate 3) was dissolved in MeOH (1 mL) and 7M ammonia in MeOH (4 mL, 28 mmol) was added. The solution was heated at 60° C. for 12 h in a sealed vial. The solution was evaporated in vacuo. The treatment with 7M ammonia was repeated in the same way one more time. Evaporation in vacuo gave the title compound (73 mg, 77% yield) which was used without further purification in the following step. 1H NMR (400 MHz, CDCl3) δ ppm 2.11 (m, 2 H), 2.35 (s, 3 H), 4.53 (m, 2 H), 4.98 (br s, 2 H), 6.66 (m, 1 H), 6.78 (d, 1 H), 7.22 (m, 1 H); MS (ES+) m/z 294 [M+H]+.

Aufarbeitung

  1. customThe solution was evaporated in vacuo
  2. customEvaporation in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-63a49884eae14fcfb68e9a492f69d021
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08865911B2

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