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

HRID 42761

반응식

HRID 42761 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.[CH3:20][C:21]1([C:26]2[CH:27]=[C:28]([CH:35]=[CH:36][CH:37]=2)[CH2:29]OS(C)(=O)=O)[O:25][CH2:24][CH2:23][O:22]1>CN(C=O)C.CC(=O)OCC.O>[CH3:20][C:21]1([C:26]2[CH:27]=[C:28]([CH:35]=[CH:36][CH:37]=2)[CH2:29][N:8]2[N:7]=[C:6]([N+:3]([O-:5])=[O:4])[CH:10]=[N:9]2)[O:22][CH2:23][CH2:24][O:25]1

참가 물질

8

반응물 4

HCID 947NitrogenHCID 81531DiisopropylethylamineHCID 2781504-nitro-2H-1,2,3-triazoleHCID 86649478(3-(2-Methyl-[1,3]dioxolan-2-yl)-phenyl)methyl methanesulfonate

생성물 1

HCID 673654222-[3-(2-Methyl-[1,3]dioxolan-2-yl)-benzyl]-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 (50 mg, 0.43 mmol) in DMF (1.0 mL) was treated with DIPEA (0.15 mL, 0.87 mmol). After 30 min, a solution of methanesulfonic acid 3-(2-methyl-[1,3]dioxolan-2-yl)-benzyl ester (106 mg, 0.52 mmol) in DMF (1.0 mL) was added and the reaction mixture was stirred for 3 days at 50° C. Water (10 mL), followed by EA (10 mL) were added. The aq. layer was extracted with EA (10 mL) and the combined org. extracts were dried over Na2SO4, filtered, and the solvents were removed under reduced pressure. Purification of the residue by FC (2:1 hept-EA) gave the title compound as a colorless oil: TLC:rf (1:2 hept-EA)=0.42. LC-MS-conditions 02: tR=0.99 min.

후처리

  1. additionwere added
  2. extractionThe aq. layer was extracted with EA (10 mL)
  3. dry with materialextracts were dried over Na2SO4
  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-5165ea9072ce49c6af505bbc9bc310b2
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08536209B2

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