반응 #685033

반응 방정식

4-methoxybenzaldehyde

tert-butyl carbazate

→

title compound

수율 102.0%

(E)-tert-Butyl 2-(4-methoxybenzylidene)hydrazinecarboxylate

수율 102.0%

용매

toluene

반응 조건

후처리

1. 1
   온도Heat
2. 2
   온도to reflux over a period of 1 hour (h)
3. 3
   기타collecting water in an azeotrope with the toluene
4. 4
   기타After no further water is collected
5. 5
   기타Add hexanes until the product precipitates from solution
6. 6
   온도Cool the bath further to 20° C
7. 7
   기타Collect the solids
8. 8
   여과by filtration
9. 9
   기타dry

실험 절차

Add 4-methoxybenzaldehyde (400 g, 2.94 mol) over 20 min to a solution of tert-butyl carbazate (400 g, 2.94 mol) in toluene (750 mL) at 50° C. Heat to reflux over a period of 1 hour (h), collecting water in an azeotrope with the toluene. After no further water is collected, cool to 60° C. Add hexanes until the product precipitates from solution. Cool the bath further to 20° C. Collect the solids by filtration and dry using a nitrogen press to afford the title compound (750.5 g, 91%). 1H NMR [400 MHz, dimethyl sulfoxide-d6 (DMSO-d6)] δ 10.6-10.8 (bs, 1H), 7.88-8.0 (S, 1H), 7.5-7.55 (d, 2H), 6.95-7.0 (d, 2H), 1.45 (s, 9H). ES/MS (m/z): 249 [M-H].

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