반응 #658152

반응 방정식

(isocyanatomethyl)(methyl)sulfane

(E)-4-(2-(4-diazo-4H-imidazol-5-yl)vinyl)benzonitrile

→

title compound

수율 8.1%

(E)-4-(2-(3-(Methylthiomethyl)-4-oxo-3,4-dihydroimidazo[5,1-d][1,2,3,5]tetrazin-8-yl)vinyl)benzonitrile

수율 8.1%

용매

DMSO

DMSO

반응 조건

후처리

1. 1
   workup.ADDITIONThe resulting solution was poured into ice
2. 2
   여과the precipitate was filtered
3. 3
   세척washed successively with water and diethyl ether
4. 4
   건조The crude product was dried under vacuum
5. 5
   기타was absorbed on silica
6. 6
   기타purified by flash chromatography

실험 절차

A solution of (isocyanatomethyl)(methyl)sulfane (337 mg, 3.27 mmol) in dry DMSO (1 mL) was added dropwise in the dark under nitrogen to a stirred suspension of (E)-4-(2-(4-diazo-4H-imidazol-5-yl)vinyl)benzonitrile (600 mg, 2.71 mmol) in DMSO (6 mL) and the mixture was stirred overnight. The resulting solution was poured into ice and the precipitate was filtered and washed successively with water and diethyl ether. The crude product was dried under vacuum and was absorbed on silica and purified by flash chromatography using DCM:MeCN (95:5) as eluent to give the pure title compound as a bright yellow solid (71 mg, 8%). δH (DMSO d6): 8.87 (1H, s), 7.94-7.97 (2H, d, J=8.6), 7.85-7.87 (2H, d, J=8.6), 7.73 (2H, s), 5.40 (2H, s), 2.27 (3H, s).

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