Nitrogen → 2-[4-(2-Methyl-[1,3]dioxolan-2-yl)-thiazol-2-ylmethyl]-2H-[1,2,3]triazol-4-ylamine

HRID 42773ノート

反応式

HRID 42773 の反応式
N#N.[CH3:3][C:4]1([C:9]2[N:10]=[C:11]([CH2:14][N:15]3[N:19]=[C:18]([N+:20]([O-])=O)[CH:17]=[N:16]3)[S:12][CH:13]=2)[O:8][CH2:7][CH2:6][O:5]1.[NH4+].[Cl-]>CCO.O.[Fe]>[CH3:3][C:4]1([C:9]2[N:10]=[C:11]([CH2:14][N:15]3[N:19]=[C:18]([NH2:20])[CH:17]=[N:16]3)[S:12][CH:13]=2)[O:5][CH2:6][CH2:7][O:8]1

参加物

7

反応物 3

HCID 947NitrogenHCID 25517Ammonium ChlorideHCID 671276452-[4-(2-methyl-[1,3]dioxolan-2-yl)-thiazol-2-ylmethyl]-4-nitro-2H-[1,2,3]triazole

生成物 1

HCID 673651222-[4-(2-Methyl-[1,3]dioxolan-2-yl)-thiazol-2-ylmethyl]-2H-[1,2,3]triazol-4-ylamine収率 92%

試薬・触媒・溶媒 3

HCID 23925Iron触媒HCID 702Ethanol溶媒HCID 962Water溶媒

反応条件

温度
75 °C

実験手順

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a mixture of 2-[4-(2-methyl-[1,3]dioxolan-2-yl)-thiazol-2-ylmethyl]-4-nitro-2H-[1,2,3]triazole (145 mg, 0.49 mmol), iron powder (83 mg, 1.46 mmol) and NH4Cl (132 mg, 2.44 mmol) in a mixture of EtOH (2.0 mL) and water (1.0 mL) was stirred at 75° C. for 1 h. The reaction mixture was filtered while hot and the filter cake rinsed with EtOH. The filtrate was concentrated under reduced pressure and the residue partitioned between CH2Cl2 (10 mL) and aq. 1M NaOH (10 mL). The aq. layer was extracted with CH2Cl2 (2×10 mL). The combined org. extracts were dried over MgSO4, filtered, and the solvent removed under reduced pressure to give the title compound as a yellow oil (120 mg, 92%). LC-MS-conditions 02: tR=0.68 min, [M+H]+=268.05.

後処理

  1. filtrationThe reaction mixture was filtered while hot and the filter cake
  2. washrinsed with EtOH
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. customthe residue partitioned between CH2Cl2 (10 mL) and aq. 1M NaOH (10 mL)
  5. extractionThe aq. layer was extracted with CH2Cl2 (2×10 mL)
  6. dry with materialextracts were dried over MgSO4
  7. filtrationfiltered
  8. customthe solvent removed under reduced pressure

出典と根拠

ORDレコード
ord-ebfe2c96f0534db9bac245440daa4ea3
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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