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

HRID 42773노트

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HRID 42773 반응식
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

참가 물질

7

반응물 3

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

생성물 1

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

시약·촉매·용매 3

HCID 23925Iron촉매HCID 702Ethanol용매HCID 962Water용매

반응 조건

온도
75 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-ebfe2c96f0534db9bac245440daa4ea3
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08536209B2

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