반응 #80119

반응 방정식

1-benzoyl-3-{2-methoxy-5-[(2-methoxy-ethyl)-methyl-amino]-phenyl}-thiourea

bromine

→

N-{4-methoxy-7-[(2-methoxy-ethyl)-methyl-amino]-benzothiazol-2-yl}-benzamide

수율 28.1%

용매

chloroform

반응 조건

후처리

1. 1
   온도the reaction mixture heated
2. 2
   온도at reflux for 18 hours
3. 3
   workup.ADDITIONpoured slowly onto water
4. 4
   추출extracted three times with ethyl acetate
5. 5
   건조The combined organic phases were dried over sodium sulfate
6. 6
   농축concentrated in vacuo

실험 절차

To a stirred solution of 430 mg (1.15 mmol) 1-benzoyl-3-{2-methoxy-5-[(2-methoxy-ethyl)-methyl-amino]-phenyl}-thiourea in 8 ml chloroform was added dropwise 0.059 ml (1.15 mmol) bromine and the reaction mixture heated at reflux for 18 hours. The mixture was then cooled to room temperature, poured slowly onto water and extracted three times with ethyl acetate. The combined organic phases were dried over sodium sulfate and concentrated in vacuo. Flash chromatography (1/4 ethyl acetate/hexane) afforded 120 mg (28%) N-{4-methoxy-7-[(2-methoxy-ethyl)-methyl-amino]-benzothiazol-2-yl}-benzamide as a yellow solid. ES-MS m/e (%): 394 (M+Na+, 14), 372 (M+H+, 100).

출처