Tetrahydrofuran → Ethyl 5-phenyl-1,3,4-thiadiazole-2-carboxylate

HRID 1424350노트

반응식

HRID 1424350 반응식
[C:1]([NH:9][NH:10][C:11](=O)[C:12]([O:14][CH2:15][CH3:16])=[O:13])(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1COCC1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:32])=CC=1>>[C:2]1([C:1]2[S:32][C:11]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[N:10][N:9]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

4

반응물 3

HCID 8028TetrahydrofuranHCID 87949Lawesson's reagent2회HCID 13013233Ethyl 2-(2-benzoylhydrazinyl)-2-oxoacetate

생성물 1

HCID 67306900Ethyl 5-phenyl-1,3,4-thiadiazole-2-carboxylate수율 56%

실험 절차

To a solution of ethyl 2-(2-benzoylhydrazinyl)-2-oxoacetate (1 g, 4.23 mmol) in dry THF (5 ml, 61.0 mmol) was added the Lawesson's Reagent (1.079 g, 2.67 mmol). The reaction was stirred at r.t. for 2 h without any reaction. The mixture was then heated to 50° C. and then heated to reflux. Additional Lawesson's Reagent (1.079 g, 2.67 mmol) was added and after 16 h at reflux, the reaction was halfway completed. The mixture was evaporated to dryness and the residue was purified by silica gel column chromatography (50% CH2Cl2/hexanes up to 100% CH2Cl2) to provide the title material (0.35 g, 35%). LC (Method B): 2.063 min, LCMS (APCI) calcd for C11H11N2O2S [M+H]+ m/z 235.05. found 235.0. 1H NMR (CDCl3, 400 MHz) δ ppm: 1.49 (t, J=1.00 Hz, 3H), 4.55 (q, J=1.00 Hz, 2H), 7.45-7.65 (m, 3H), 8.02-8.07 (m, 2H).

후처리

  1. temperatureThe mixture was then heated to 50° C.
  2. temperatureheated to reflux
  3. temperatureat reflux
  4. customThe mixture was evaporated to dryness
  5. customthe residue was purified by silica gel column chromatography (50% CH2Cl2/hexanes up to 100% CH2Cl2)

출처 및 근거

ORD 기록
ord-fce95a84e9a442d382a4e98aebd65180
출처 데이터셋
uspto-grants-2015_01
특허 번호
US08927688B2

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