Triethylamine → N-(2-Hydroxy-4-nitrophenyl)-N'-(2-benzyloxypropyl)urea

HRID 368382

Reaktionsgleichung

Reaktionsgleichung von HRID 368382
[Si]([O:8][C:9]1[CH:15]=[C:14]([N+:16]([O-:18])=[O:17])[CH:13]=[CH:12][C:10]=1[NH2:11])(C(C)(C)C)(C)C.Cl[C:20](Cl)([O:22]C(=O)OC(Cl)(Cl)Cl)Cl.C(N(CC)CC)C.[CH2:38]([O:45][CH:46]([CH3:49])[CH2:47][NH2:48])[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1>C1(C)C=CC=CC=1>[OH:8][C:9]1[CH:15]=[C:14]([N+:16]([O-:18])=[O:17])[CH:13]=[CH:12][C:10]=1[NH:11][C:20]([NH:48][CH2:47][CH:46]([O:45][CH2:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)[CH3:49])=[O:22]

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 94429TriphosgeneHCID 2960152-(Benzyloxy)propan-1-amineHCID 154857102-[(Tert-butyldimethylsilyl)oxy]-4-nitroaniline

Produkt 1

HCID 15485714N-(2-Hydroxy-4-nitrophenyl)-N'-(2-benzyloxypropyl)ureaAusbeute 103 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a solution of 2-tert-butyldimethylsilyloxy-4-nitroaniline (300 mg, 1.125 mmol) in toluene (10 mL), triphosgene (126 mg, 0.45 mmol) and triethylamine (0.195 mL, 1.35 mmol) were added. The reaction mixture was stirred at 80° C. for 3 hours. Then it was cooled to room temperature and all solvent was evaporated. The residue was dissolved in DMF (1 mL) and 2-benzyloxypropylamine (185.6 mg, 1.125 mmol) was added. The reaction mixture was stirred at 80° C. for 16 hours. Chromatography of the resulting liquid on silica gel (50% Ethyl acetate/Hexane) gave desired product (160 mg, 41%). EI-MS m/z 346.4 (M+). mp: 64.6-65.2° C.

Aufarbeitung

  1. temperatureThen it was cooled to room temperature
  2. customall solvent was evaporated
  3. dissolutionThe residue was dissolved in DMF (1 mL)
  4. stirringThe reaction mixture was stirred at 80° C. for 16 hours

Quellen und Nachweise

ORD-Eintrag
ord-07e213e56cea42cebb574def8e748fdd
Quelldatensatz
uspto-grants-2000_10
Patentnummer
US06133319

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