Ethyl 3-ethoxy-3-iminopropionate hydrochloride → Ethyl 2-(5-amino-1,3,4-thiadiazol-2-yl)acetate

HRID 631050

反応式

HRID 631050 の反応式
[NH2:1][NH:2][C:3]([NH2:5])=[S:4].Cl.C(O[C:10](=N)[CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])C>>[NH2:5][C:3]1[S:4][C:10]([CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])=[N:1][N:2]=1

参加物

3

反応物 2

HCID 75345Ethyl 3-ethoxy-3-iminopropionate hydrochlorideHCID 2723789Thiosemicarbazide

生成物 1

HCID 292304Ethyl 2-(5-amino-1,3,4-thiadiazol-2-yl)acetate収率 47%

反応条件

温度
5 °C

実験手順

Thiosemicarbazide (1.0 g, 11.0 mmol) and ethyl 3-ethoxy-3-iminopropionate hydrochloride (2.0 g, 10.0 mmol) were mixed in glacial acid (2 mL) for 10 min at 55° C. and then boiled for 1.5 h. The reaction mixture was evaporated, diluted with cold water, carefully neutralized with NaHCO3, and cooled to 5° C. The precipitate was collected and crystallized from water to yield 0.88 g (4.70 mmol, 47%) of the product, mp 149-150° C.; 1H NMR (300 MHz, DMSO-d6) δ 1.19 (t, 3H, J=7.2 Hz), 3.96 (s, 2H), 4.10 (q, 2H, J=6.9 Hz), 7.11 (s, 2H); 13C NMR (75 MHz, DMSO-d6) δ 14.0, 35.4, 60.9, 150.4, 168.9, 169.6.

後処理

  1. customThe reaction mixture was evaporated
  2. additiondiluted with cold water
  3. customThe precipitate was collected
  4. customcrystallized from water

出典と根拠

ORDレコード
ord-c35730d6175f415182ab9fe957aec0f7
出典データセット
uspto-grants-2016_04
特許番号
US09320734B2

関連ノート

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