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

HRID 42751

반응식

HRID 42751 반응식
N#N.[N+:3]([C:6]1[CH:10]=[N:9][NH:8][N:7]=1)([O-:5])=[O:4].C([O-])([O-])=O.[Cs+].[Cs+].Br[CH2:18][CH2:19][CH2:20][CH2:21][C:22]1([CH3:27])[O:26][CH2:25][CH2:24][O:23]1>C(C#N)(C)=O.CC(=O)OCC.O>[CH3:27][C:22]1([CH2:21][CH2:20][CH2:19][CH2:18][N:8]2[N:7]=[C:6]([N+:3]([O-:5])=[O:4])[CH:10]=[N:9]2)[O:26][CH2:25][CH2:24][O:23]1

참가 물질

8

반응물 4

HCID 947NitrogenHCID 10796Cesium carbonateHCID 2781504-nitro-2H-1,2,3-triazoleHCID 5600132-(4-Bromobutyl)-2-methyl-1,3-dioxolane

생성물 1

HCID 673657742-[4-(2-Methyl-[1,3]dioxolan-2-yl)-butyl]-4-nitro-2H-[1,2,3]triazole

시약·촉매·용매 3

HCID 962Water용매HCID 8857Ethyl Acetate용매HCID 694302-Oxopropiononitrile용매2회

반응 조건

온도
80 °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 (100 mg, 0.88 mmol) and Cs2CO3 (315 mg, 0.96 mmol) in AcCN (1.0 mL) was treated with a solution of 2-(4-bromo-butyl)-2-methyl-[1,3]dioxolane (215 mg, 0.96 mmol) in AcCN (1.0 mL). The reaction mixture was stirred at 80° C. for 16 h. Water (20 mL), followed by EA (30 mL) were added. The aq. layer was extracted with EA (30 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: TLC:rf (2:1 hept-EA)=0.33. LC-MS-conditions 02: tR=0.92 min.

후처리

  1. additionwere added
  2. extractionThe aq. layer was extracted with EA (30 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-13f14351087a423995aa1bab4fb8feb8
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08536209B2

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