Water → N-[(4-Fluoro-3-nitrophenyl)carbamoyl]glycine, ethyl ester

HRID 363166

Reaktionsgleichung

Reaktionsgleichung von HRID 363166
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]=[C:9]=[O:10])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12].Cl.[CH2:15]([O:17][C:18](=[O:21])[CH2:19][NH2:20])[CH3:16].C(N(CC)CC)C.O>O1CCCC1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([NH:20][CH2:19][C:18]([O:17][CH2:15][CH3:16])=[O:21])=[O:10])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12]

Komponenten

6

Edukt 4

HCID 962WaterHCID 8471TriethylamineHCID 1441174-Fluoro-3-nitrophenyl isocyanateHCID 2723640Glycine ethyl ester, hydrochloride

Produkt 1

HCID 85708209N-[(4-Fluoro-3-nitrophenyl)carbamoyl]glycine, ethyl esterAusbeute 56,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of 4-fluoro-3-nitrophenyl isocyanate (10 g, 0.055 mol) in anhydrous tetrahydrofuran is cooled to 0° C., treated with glycine ethyl ester hydrochloride (7.7 g, 0.055 mol), treated with triethylamine (5.56 g, 0.055 mol) while maintaining the temperature below 100° C., stirred at room temperature for 1 hour and poured into water. The aqueous mixture is extracted with ether. The combined organic extracts are washed sequentially with 1N hydrochloric acid and brine, dried over anhydrous, magnesium sulfate, and concentrated in vacuo to obtain a solid which is air-dried to give the title product as a yellow solid (8.8 g, mp 115°-120° C.).

Aufarbeitung

  1. temperaturewhile maintaining the temperature below 100° C.
  2. extractionThe aqueous mixture is extracted with ether
  3. washThe combined organic extracts are washed sequentially with 1N hydrochloric acid and brine
  4. dry with materialdried over anhydrous, magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customto obtain a solid which
  7. customis air-dried

Quellen und Nachweise

ORD-Eintrag
ord-f1fe8bc5cbd84f3ca2ce9234f76f87e5
Quelldatensatz
uspto-grants-1999_02
Patentnummer
US05872253

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