Water → 1-Amino-2-(benzyloxy)-4-methylpyridinium 2,4,6-trimethylbenzenesulphonate

HRID 1486238Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1486238
FC(F)(F)C(O)=O.O.[C:9]1([CH3:27])[CH:14]=[C:13]([CH3:15])[CH:12]=[C:11]([CH3:16])[C:10]=1[S:17]([O:20]/[N:21]=C(/OCC)\C)(=[O:19])=[O:18].[CH2:28]([O:35][C:36]1[CH:41]=[C:40]([CH3:42])[CH:39]=[CH:38][N:37]=1)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>ClCCl.C(OCC)C>[CH3:16][C:11]1[CH:12]=[C:13]([CH3:15])[CH:14]=[C:9]([CH3:27])[C:10]=1[S:17]([O-:20])(=[O:19])=[O:18].[NH2:21][N+:37]1[CH:38]=[CH:39][C:40]([CH3:42])=[CH:41][C:36]=1[O:35][CH2:28][C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1

Komponenten

7

Edukt 4

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 6282444Ethyl O-MesitylsulfonylacetohydroxamateHCID 142234762-(Benzyloxy)-4-methylpyridine

Produkt 1

HCID 1178578501-Amino-2-(benzyloxy)-4-methylpyridinium 2,4,6-trimethylbenzenesulphonateAusbeute 47,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
-5 °C

Versuchsvorschrift

A mixture of 18.0 ml of trifluoroacetic acid (233 mmol, 10 eq.) and 2.66 ml of water was cooled to −5° C. At this temperature, 9.99 g (35.0 mmol, 1.5 eq.) of ethyl (1E)-N-[(mesitylsulphonyl)oxy]ethanimidoate [CAS No: 38202-27-6] were added in portions. After 1.5 h, 150 ml of ice-water were added, and the mixture was stirred briefly and extracted with 100 ml of dichloromethane. The organic phase was dried with magnesium sulphate and filtered, and the resulting solution of O-(2-mesitylenesulphonyl)hydroxylamine (MSH) was added dropwise directly to a solution, cooled to 0° C., of 4.65 g (23.3 mmol, 1.0 eq.) of 2-(benzyloxy)-4-methylpyridine from Example 5A in 50 ml of dichloromethane. The mixture was stirred at RT for 2 h. Subsequently, 1 l of diethyl ether was added dropwise, and precipitated solids were filtered off, washed with 250 ml of diethyl ether and dried. 4.6 g of the title compound were isolated (48% of theory).

Aufarbeitung

  1. extractionextracted with 100 ml of dichloromethane
  2. dry with materialThe organic phase was dried with magnesium sulphate
  3. filtrationfiltered
  4. additionthe resulting solution of O-(2-mesitylenesulphonyl)hydroxylamine (MSH) was added dropwise directly to a solution
  5. stirringThe mixture was stirred at RT for 2 h
  6. customprecipitated solids
  7. filtrationwere filtered off
  8. washwashed with 250 ml of diethyl ether
  9. customdried

Quellen und Nachweise

ORD-Eintrag
ord-861639ceb275422697abb3179635dc0d
Quelldatensatz
uspto-grants-2016_08
Patentnummer
US09422285B2

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