Nitrogen → 6-(4-Nitro-[1,2,3]triazol-2-yl)-hexan-2-one

HRID 42763노트

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HRID 42763 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.Br[CH2:21][CH2:22][CH2:23][CH2:24][C:25](=[O:27])[CH3:26]>CN(C=O)C.CC(=O)OCC.O>[N+:3]([C:6]1[CH:10]=[N:9][N:8]([CH2:21][CH2:22][CH2:23][CH2:24][C:25](=[O:27])[CH3:26])[N:7]=1)([O-:5])=[O:4]

참가 물질

8

반응물 4

HCID 947NitrogenHCID 250616-Bromohexan-2-oneHCID 81531DiisopropylethylamineHCID 2781504-nitro-2H-1,2,3-triazole

생성물 1

HCID 673652636-(4-Nitro-[1,2,3]triazol-2-yl)-hexan-2-one

시약·촉매·용매 3

HCID 962Water용매HCID 6228Dimethylformamide용매2회HCID 8857Ethyl Acetate용매

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온도
50 °C

실험 절차

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a suspension of 4-nitro-2H-[1,2,3]triazole (114 mg, 1.00 mmol) in DMF (1.0 mL) was treated with DIPEA (0.34 mL, 2.00 mmol). After 30 min, a solution of 6-bromo-hexan-2-one (179 mg, 1.00 mmol) in DMF (1.0 mL) was added and the reaction mixture was stirred for 24 h 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 yellow oil: TLC:rf (2:1 hept-EA)=0.26. LC-MS-conditions 02: tR=0.86 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-5e25961a1c2a4638ac66cb199ce37e90
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08536209B2

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