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

HRID 42763

反応式

HRID 42763 の反応式
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]

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒2 回HCID 8857Ethyl Acetate溶媒

反応条件

温度
50 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-5e25961a1c2a4638ac66cb199ce37e90
出典データセット
uspto-grants-2013_09
特許番号
US08536209B2

関連ノート

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