Nitrogen → 2-[5-(2-Methyl-[1,3]dioxolan-2-yl)-furan-2-yl]-thioacetamide

HRID 1189427노트

반응식

HRID 1189427 반응식
N#N.C[Si](C)(C)[S:5][Si](C)(C)C.C[O-].[Na+].[CH3:15][C:16]1([C:21]2[O:25][C:24]([CH2:26][C:27]#[N:28])=[CH:23][CH:22]=2)[O:20][CH2:19][CH2:18][O:17]1>CN(C=O)C.O>[CH3:15][C:16]1([C:21]2[O:25][C:24]([CH2:26][C:27]([NH2:28])=[S:5])=[CH:23][CH:22]=2)[O:17][CH2:18][CH2:19][O:20]1

참가 물질

7

반응물 4

HCID 947NitrogenHCID 76920Disilathiane, 1,1,1,3,3,3-hexamethyl-HCID 10942334Sodium MethoxideHCID 67128458[5-(2-Methyl-[1,3]dioxolan-2-yl)-furan-2-yl]-acetonitrile

생성물 1

HCID 866649202-[5-(2-Methyl-[1,3]dioxolan-2-yl)-furan-2-yl]-thioacetamide

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매2회

실험 절차

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), hexamethyldisilthiane (9.45 mL, 45.07 mmol) was added dropwise to a solution of NaOMe (2.51 g, 45.07 mmol) in dry DMF (40 mL) and the reaction mixture was stirred at rt for 15 min. This dark blue solution was then added to a solution of [5-(2-methyl-[1,3]dioxolan-2-yl)-furan-2-yl]-acetonitrile (3.48 g, 18.03 mmol) in DMF (30 mL) and the reaction mixture was stirred for 16 h at rt. Water (300 mL) was then added and the mixture was extracted twice with EA (300 mL). The combined org. phases were dried over MgSO4, filtered, and the solvent was removed under reduced pressure. Purification of the residue by FC (6:4 hept-EA) gave the title compound as a yellow oil. TLC: rf (6:4 hept-EA)=0.18. LC-MS-conditions 02: tR=0.74 min, [M+H]+=228.44.

후처리

  1. stirringthe reaction mixture was stirred for 16 h at rt
  2. extractionthe mixture was extracted twice with EA (300 mL)
  3. dry with materialphases were dried over MgSO4
  4. filtrationfiltered
  5. customthe solvent was removed under reduced pressure
  6. customPurification of the residue by FC (6:4 hept-EA)

출처 및 근거

ORD 기록
ord-1ba0fd3315d846eaa2195df73a910dad
출처 데이터셋
uspto-grants-2014_03
특허 번호
US08674111B2

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