Dibromomethane → 1,1-Bis[4-[n,n-bis[4,6-dichloro-1,3,5-triazin-2-yl]amino]phenoxy]methane

HRID 8419

Reaktionsgleichung

Reaktionsgleichung von HRID 8419
[N:1]1[C:8](Cl)=[N:7][C:5]([Cl:6])=[N:4][C:2]=1[Cl:3].[NH2:10][C:11]1[CH:26]=[CH:25][C:14]([O:15][CH2:16][O:17][C:18]2[CH:23]=[CH:22][C:21]([NH2:24])=[CH:20][CH:19]=2)=[CH:13][CH:12]=1.BrCBr.[H-].[Na+]>O1CCCC1>[Cl:6][C:5]1[N:4]=[C:2]([Cl:3])[N:1]=[C:8]([N:24]([C:21]2[CH:22]=[CH:23][C:18]([O:17][CH2:16][O:15][C:14]3[CH:25]=[CH:26][C:11]([N:10]([C:8]4[N:7]=[C:5]([Cl:6])[N:4]=[C:2]([Cl:3])[N:1]=4)[C:8]4[N:7]=[C:5]([Cl:6])[N:4]=[C:2]([Cl:3])[N:1]=4)=[CH:12][CH:13]=3)=[CH:19][CH:20]=2)[C:8]2[N:7]=[C:5]([Cl:6])[N:4]=[C:2]([Cl:3])[N:1]=2)[N:7]=1

Komponenten

6

Edukt 4

HCID 3024DibromomethaneHCID 7954Cyanuric chlorideHCID 24758Sodium hydrideHCID 602344-[(4-Aminophenoxy)methoxy]aniline

Produkt 1

HCID 220154401,1-Bis[4-[n,n-bis[4,6-dichloro-1,3,5-triazin-2-yl]amino]phenoxy]methaneAusbeute 16 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

Cyanuric chloride (11.473 grams, 62.2 mmol) in dry tetrahydrofuran (50 milliliters) was added to a solution of 1,1-bis(4-aminophenoxy)methane (3.58 grams, 15.55 mmol; prepared as described in Part B of Example VIII except that 1,1-dibromomethane was used instead of 1,5-dibromopentane) in dry tetrahydrofuran (175 milliliters) at −10° C. The mixture was stirred for 10 minutes and sodium hydride (3.75 grams, 93.3 mmol) was added dropwise. The mixture was then heated to 60° C. for 16 hours and subsequently filtered on CELITE. The volatiles were removed under reduced pressure and the crude solid was purified on silica gel using a mixture of AcOEt/hexane (3:7, v/v) as eluant to afford pure 1,1-bis[4-[N,N-bis[4,6-dichloro-1,3,5-triazin-2-yl]amino]phenoxy]methane (2.10 grams, 2.55 mmol, 16 percent yield) as a white solid. Chromatography with silica gel is believed to be responsible for the low yield.

Aufarbeitung

  1. customprepared
  2. customat −10° C
  3. filtrationsubsequently filtered on CELITE
  4. customThe volatiles were removed under reduced pressure
  5. customthe crude solid was purified on silica gel using
  6. additiona mixture of AcOEt/hexane (3:7, v/v) as eluant

Quellen und Nachweise

ORD-Eintrag
ord-15b09eaac7d0451581148c6eef1c9bd2
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07087752B2

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