反応 #1884992

反応方程式

tert-butylamine

acetonitrile

tert-butyl chloride

NaOH

→

N,N′-di-tert-butyl acetamidine

溶媒

CH2Cl2

water

反応条件

後処理

1. 1
   温度While the solution was cooled below −70° C.
2. 2
   workup.WAITThe solution was then left
3. 3
   workup.STIRRINGstirring at −70° C. for a few hours
4. 4
   温度warmed up to −20° C.
5. 5
   その他The organic layer was separated
6. 6
   抽出the aqueous phase was then extracted with fresh CH2Cl2
7. 7
   洗浄Combined CH2Cl2 fractions were washed twice with water
8. 8
   乾燥dried over anhydrous MgSO4
9. 9
   その他The dried organic solution was evaporated
10. 10
    その他to yield a light yellow liquid

実験手順

N,N′-di-tert-butyl acetamidine was synthesized as follows. Anhydrous FeCl3 (1.04 mol.) was suspended in 1 L of CH2Cl2 under N2 at room temperature. The suspension was cooled to −40 to −50° C. and acetonitrile (1 mol) was quickly added with stirring. While the solution was cooled below −70° C., tert-butyl chloride (1.04 mol) was added, followed by tert-butylamine (1.05 mol). The solution was then left stirring at −70° C. for a few hours and then warmed up to −20° C., followed by pouring it into a diluted aqueous NaOH solution (12.5 wt %, 1 L). Additional water was added to ensure complete formation of precipitate. The organic layer was separated and the aqueous phase was then extracted with fresh CH2Cl2. Combined CH2Cl2 fractions were washed twice with water and dried over anhydrous MgSO4. The dried organic solution was evaporated to yield a light yellow liquid. The crude amidine thus obtained was then purified by fractional distillation. Yield of the main fraction was >70%, and free of organic and metallic impurities as detected by 1H NMR and ICP-MS. 1H NMR (in C6D6, δ ppm): 3.02 (br. s, 1H), 1.41 (s, 3H), δ 1.34 (s, 18H).

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