反応 #8515

反応方程式

sodium hydride

1,1-dibromomethane

Cyanuric chloride

1,1-bis(4-aminophenoxy)methane

→

1,1-bis[4-[N,N-bis[4,6-dichloro-1,3,5-triazin-2-yl]amino]phenoxy]methane

収率 16.0%

溶媒

tetrahydrofuran

tetrahydrofuran

反応条件

後処理

1. 1
   その他prepared
2. 2
   その他at −10° C
3. 3
   ろ過subsequently filtered on CELITE
4. 4
   その他The volatiles were removed under reduced pressure
5. 5
   その他the crude solid was purified on silica gel using
6. 6
   workup.ADDITIONa mixture of AcOEt/hexane (3:7, v/v) as eluant

実験手順

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.

出典