4-Chlorophenylhydroxylamine → N'-[4,6-bis(2,2,2-trifluoroethoxy)pyrimidin-2-yl]-N-(4chlorophenyl)-N-hydroxyurea

HRID 907421

Reaktionsgleichung

Reaktionsgleichung von HRID 907421
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([NH:6][OH:7])=[CH:4][CH:3]=1.[N:10]([C:13]1[N:18]=[C:17]([O:19][CH2:20][C:21]([F:24])([F:23])[F:22])[CH:16]=[C:15]([O:25][CH2:26][C:27]([F:30])([F:29])[F:28])[N:14]=1)=[C:11]=[O:12]>C1COCC1>[F:24][C:21]([F:22])([F:23])[CH2:20][O:19][C:17]1[CH:16]=[C:15]([O:25][CH2:26][C:27]([F:28])([F:29])[F:30])[N:14]=[C:13]([NH:10][C:11](=[O:12])[N:6]([C:5]2[CH:8]=[CH:9][C:2]([Cl:1])=[CH:3][CH:4]=2)[OH:7])[N:18]=1

Komponenten

4

Edukt 2

HCID 699834-ChlorophenylhydroxylamineHCID 576517972-Isocyanato-4,6-bis(2,2,2-trifluoroethoxy)pyrimidine

Produkt 1

HCID 57651739N'-[4,6-bis(2,2,2-trifluoroethoxy)pyrimidin-2-yl]-N-(4chlorophenyl)-N-hydroxyureaAusbeute 36 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a solution of 4-chloro-N-hydroxyaniline (0.423 g, 2.95 mmol (prepared according to the procedure of Rondestwedt Jr., C. S. and Johnson, T. A. Synthesis 1977, p850-851) in THF (10 mL) was added the 2-isocyanato-4,6-bis(2,2,2-trifluoroethoxy)pyrimidine (2.0 g, 6.3 mmol) in THF (10 mL) and the mixture stirred at room temperature for 12 h. The mixture was concentrated in vacuo to give a brown solid. This solid was purified by reverse phase column chromatography (CH3CN/H2O) to afford 64 as a dark brown gum (448 mg, 36% yield): ESI/MS 461 (M+H), 459 (M−H); 1H NMR (DMSO-d6): δ 11.04 (S, 1H, 9.51 (S, 1H), 7.63 (d, 2H, J=6.6 Hz), 7.41 (d, 2H, J=6.6 Hz), 6.30 (s, 1H), 5.05 (m, 4H).

Aufarbeitung

  1. customSynthesis 1977
  2. concentrationThe mixture was concentrated in vacuo
  3. customto give a brown solid
  4. customThis solid was purified by reverse phase column chromatography (CH3CN/H2O)

Quellen und Nachweise

ORD-Eintrag
ord-704cbc43b9494840a316f8238e7cfca6
Quelldatensatz
uspto-grants-2011_09
Patentnummer
US08013154B2

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