반응 #1483049

반응 방정식

sodium nitrite

4-(hydroxymethyl)-benzenecarboximidic acid, ethyl ester, hydrochloride

formamidine acetate

hydrazine

→

(4-(1,2,4,5-tetrazin-3-yl)phenyl)methanol

수율 21.3%

용매

acetic acid

water

반응 조건

후처리

1. 1
   workup.STIRRINGto stir for 15 minutes
2. 2
   기타The aqueous crude reaction
3. 3
   추출was subsequently extracted with methylene chloride (4×10 mL)
4. 4
   건조The organic extracts were dried with MgSO4
5. 5
   기타After solvent removal
6. 6
   기타the crude pink product was purified by flash chromatography (silica gel)
7. 7
   세척first washing with 100% methylene chloride

실험 절차

To a mixture of 4-(hydroxymethyl)-benzenecarboximidic acid, ethyl ester, hydrochloride (1 mmol, 216 mg) and formamidine acetate (5 mmol, 521 mg) was added anhydrous hydrazine (20 mmol, 630 uL) the resulting viscous oil was allowed to stir. After 1 hour, acetic acid (3 mL) was added followed by sodium nitrite (690 mg, 10 mmol) as a finely divided powder. The now bright pink solution was allowed to stir for 15 minutes and then diluted with 15 mL of water. The aqueous crude reaction was subsequently extracted with methylene chloride (4×10 mL). The organic extracts were dried with MgSO4. After solvent removal, the crude pink product was purified by flash chromatography (silica gel) first washing with 100% methylene chloride, followed by methylene chloride with 1% methanol, giving (4-(1,2,4,5-tetrazin-3-yl)phenyl)methanol (40 mg, 21%) as a bright pink solid. LRMS-ESI [M+H]− calcd. for C9H9N4O−: 189.08, found: 188.8.

출처