Nitrogen → 2-[5-(2-Methyl-[1,3]dioxolan-2-yl)-furan-2-ylmethyl]-4-nitro-2H-[1,2,3]triazole

HRID 42749

반응식

HRID 42749 반응식
N#N.[N+:3]([C:6]1[CH:10]=[N:9][NH:8][N:7]=1)([O-:5])=[O:4].CCN(C(C)C)C(C)C.Cl[CH2:21][C:22]1[O:26][C:25]([C:27]2([CH3:32])[O:31][CH2:30][CH2:29][O:28]2)=[CH:24][CH:23]=1>CN(C=O)C.CC(=O)OCC.O>[CH3:32][C:27]1([C:25]2[O:26][C:22]([CH2:21][N:8]3[N:7]=[C:6]([N+:3]([O-:5])=[O:4])[CH:10]=[N:9]3)=[CH:23][CH:24]=2)[O:28][CH2:29][CH2:30][O:31]1

참가 물질

8

반응물 4

HCID 947NitrogenHCID 81531DiisopropylethylamineHCID 2781504-nitro-2H-1,2,3-triazoleHCID 669289652-(5-Chloromethyl-furan-2-yl)-2-methyl-[1,3]dioxolane

생성물 1

HCID 673650422-[5-(2-Methyl-[1,3]dioxolan-2-yl)-furan-2-ylmethyl]-4-nitro-2H-[1,2,3]triazole

시약·촉매·용매 3

HCID 962Water용매HCID 6228Dimethylformamide용매2회HCID 8857Ethyl Acetate용매

반응 조건

온도
50 °C

실험 절차

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of 4-nitro-2H-[1,2,3]triazole (875 mg, 7.67 mmol) in DMF (7.0 mL) was treated at rt with DIPEA (2.63 mL, 15.34 mmol). After 30 min, a solution of 2-(5-chloromethyl-furan-2-yl)-2-methyl-[1,3]dioxolane (1.87 g, 9.21 mmol) in DMF (7.0 mL) was added and the reaction mixture was stirred for 16 h at 50° C. Water (100 mL), followed by EA (100 mL) were added. The aq. layer was extracted with EA (100 mL) and the combined org. extracts were dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Purification of the residue by FC (2:1 hept-EA) gave the title compound as an orange oil: TLC:rf (2:1 hept-EA)=0.26. LC-MS-conditions 02: tR=0.95 min; [M+H]+=281.01.

후처리

  1. additionwere added
  2. extractionThe aq. layer was extracted with EA (100 mL)
  3. dry with materialextracts were dried over MgSO4
  4. filtrationfiltered
  5. customthe solvents were removed under reduced pressure
  6. customPurification of the residue by FC (2:1 hept-EA)

출처 및 근거

ORD 기록
ord-21c32ddc19904a78b0953f41777057d9
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08536209B2

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