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

HRID 42751

反応式

HRID 42751 の反応式
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

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒HCID 694302-Oxopropiononitrile溶媒2 回

反応条件

温度
80 °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 (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.

後処理

  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)

出典と根拠

ORDレコード
ord-13f14351087a423995aa1bab4fb8feb8
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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