Hydrochloric Acid → 1-Ethyl-3-[(ethyloxy)methyl]-1H-pyrazol-5-amine

HRID 62522ノート

反応式

HRID 62522 の反応式
[CH2:1]([O:3][CH2:4][C:5](=O)[CH2:6][C:7]#[N:8])[CH3:2].C(O)(=O)C(O)=O.[CH2:16]([NH:18][NH2:19])[CH3:17].Cl>C(O)C>[CH2:16]([N:18]1[C:7]([NH2:8])=[CH:6][C:5]([CH2:4][O:3][CH2:1][CH3:2])=[N:19]1)[CH3:17]

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 96181Hydrazine, ethyl-, ethanedioate (1:1)HCID 575169104-Ethoxy-3-oxobutanenitrile

生成物 1

HCID 575169111-Ethyl-3-[(ethyloxy)methyl]-1H-pyrazol-5-amine収率 51.6%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

To a 25 mL round bottom was added 4-(ethyloxy)-3-oxobutanenitrile (550 mg, 4.33 mmol), ethyl hydrazine oxalate (641 mg, 4.33 mmol), and HCl (2.163 mL, 4.33 mmol) in ethanol (10 mL). The reaction mixture was stirred at the room temperature overnight. The reaction mixture was then evaporated, and partitioned between 20 mL of ethyl acetate and 20 mL of 1 M Na2CO3. The organic layer was washed with brine, filtered and evaporated. 1-Ethyl-3-[(ethyloxy)methyl]-1H-pyrazol-5-amine (420 mg, 2.234 mmol, 51.6% yield) was isolated as yellow oil. The product was used in the next step without further purification. LCMS (M+H)+=170.1 (M+H); 1H NMR (400 MHz, DMSO-d6) ppm 1.08 (t, J=6.95 Hz, 3 H) 1.19 (t, J=7.07 Hz, 3 H) 3.37-3.43 (m, 2 H) 3.81 (q, J=7.24 Hz, 2 H) 4.15 (s, 2 H) 5.09 (s, 2 H) 5.22 (s, 1 H).

後処理

  1. customThe reaction mixture was then evaporated
  2. custompartitioned between 20 mL of ethyl acetate and 20 mL of 1 M Na2CO3
  3. washThe organic layer was washed with brine
  4. filtrationfiltered
  5. customevaporated

出典と根拠

ORDレコード
ord-7385e4c7750341ceadf0ce305a7bca18
出典データセット
uspto-grants-2016_09
特許番号
US09446034B2

反応ノート

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