Hydrochloric Acid → 1-ethyl-5-methyl-1H-[1,2,4]triazole-3-carbaldehyde

HRID 1438339ノート

反応式

HRID 1438339 の反応式
C([O:3][CH:4](OCC)[C:5]1[N:9]=[C:8]([CH3:10])[N:7]([CH2:11][CH3:12])[N:6]=1)C.Cl>O>[CH2:11]([N:7]1[C:8]([CH3:10])=[N:9][C:5]([CH:4]=[O:3])=[N:6]1)[CH3:12]

参加物

4

反応物 2

HCID 313Hydrochloric AcidHCID 587640403-(diethoxymethyl)-1-ethyl-5-methyl-1H-1,2,4-triazole

生成物 1

HCID 587640521-ethyl-5-methyl-1H-[1,2,4]triazole-3-carbaldehyde収率 26.4%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

A mixture of 3-(diethoxymethyl)-1-ethyl-5-methyl-1H-[1,2,4]triazole from step 1 (56.86 g, 0.267 mol) and H2O (300 mL) was treated slowly with 35% aqueous HCl (55.61 g, 0.534 mol), and the reaction was stirred at room temperature for 24 h. The mixture was washed with DCM (2×200 mL). The aqueous phase was basified to pH 13 with NaOH, and washed with DCM (3×200 mL). The combined DCM extracts were discarded. The aqueous phase was neutralized to pH 7 with HCl, and extracted with DCM (3×200 mL). The organic phase from this last extraction, containing the product, was dried over Na2SO4, and the solvent was removed under vacuum, affording 9.8 g (26%) of 1-ethyl-5-methyl-1H-[1,2,4]triazole-3-carbaldehyde which was 96% pure by NMR. 1H NMR (500 MHz, CDCl3): δ 1.49 (t, J=7.5 Hz, 3H), 2.51 (s, 3H), 4.20 (q, J=7.5 Hz, 2H), 9.91 (s, 1H). 13C NMR (125 MHz, CDCl3): δ 12.1, 14.9, 44.4, 154.0, 159.2, 184.0. LC-MS (APCI) calcd for C6H9N3O: 139.07, found (M+H+): 140.1 m/z. Anal calcd for C6H9N3O: C, 51.79; H, 6.52; N, 30.20. Found: C, 51.5; H, 6.38; N, 29.98.

後処理

  1. washThe mixture was washed with DCM (2×200 mL)
  2. washwashed with DCM (3×200 mL)
  3. extractionextracted with DCM (3×200 mL)
  4. extractionThe organic phase from this last extraction
  5. additioncontaining the product
  6. dry with materialwas dried over Na2SO4
  7. customthe solvent was removed under vacuum

出典と根拠

ORDレコード
ord-9a05caefb0644b48b4011310fe0454a0
出典データセット
uspto-grants-2009_11
特許番号
US07622605B2

反応ノート

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