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

HRID 42749ノート

反応式

HRID 42749 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.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

参加物

8

反応物 4

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

生成物 1

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

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 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.

後処理

  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)

出典と根拠

ORDレコード
ord-21c32ddc19904a78b0953f41777057d9
出典データセット
uspto-grants-2013_09
特許番号
US08536209B2

反応ノート

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