Bromine → Methyl 2-(5-ethoxycarbonylamino-1,2,4-thiadiazol-3-yl)-bromoacetate

HRID 2085986ノート

反応式

HRID 2085986 の反応式
[CH2:1]([O:3][C:4]([NH:6][C:7]1[S:11][N:10]=[C:9]([CH2:12][C:13]([O:15][CH3:16])=[O:14])[N:8]=1)=[O:5])[CH3:2].[Br:17]Br>CO>[CH2:1]([O:3][C:4]([NH:6][C:7]1[S:11][N:10]=[C:9]([CH:12]([Br:17])[C:13]([O:15][CH3:16])=[O:14])[N:8]=1)=[O:5])[CH3:2]

参加物

4

反応物 2

HCID 24408BromineHCID 227269321,2,4-Thiadiazole-3-acetic acid, 5-[(ethoxycarbonyl)amino]-, methyl ester

生成物 1

HCID 22726864Methyl 2-(5-ethoxycarbonylamino-1,2,4-thiadiazol-3-yl)-bromoacetate収率 86.7%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒2 回

反応条件

温度
0 °C

実験手順

Into a 1 L round bottom flask was charged methyl 2-(5-ethoxycarbonylamino-1,2,4-thiadiazol-3-yl)acetate (50.0 g, 0.204 mol, 1.0 eq) followed by methanol (500 mL). The resulting slurry was cooled to 0° C. To the cooled slurry was charged a pre-made solution of bromine (9.9 mL, 0.194 mol, 0.95 eq) in methanol (100 mL) dropwise over 30 minutes maintaining the temperature between 0-5° C. The cold bath was removed and the solution was allowed to warm to room temperature and stirred for two hours. Proton NMR analysis of the reaction mixture showed reaction completion. The orange solution was evaporated to an orange oil. The orange oil was taken up in diethyl ether (400 mL) and the organic was washed with water (2×100 mL), saturated 1:1 NaHCO3/Na2S2O4 (2×100 mL) and then brine (100 mL). The clear colorless ether layer was dried with sodium sulfate, filtered and evaporated in vacuo to give 54.5 grams of the title compound as a clear colourless oil. 1H NMR (CDCl3) δ 1.38 (t, 3H); 3.98 (s, 3H); 4.55 (q, 2H); 5.81 (s, 1H).

後処理

  1. temperaturemaintaining the temperature between 0-5° C
  2. customThe cold bath was removed
  3. temperatureto warm to room temperature
  4. customreaction completion
  5. customThe orange solution was evaporated to an orange oil
  6. washthe organic was washed with water (2×100 mL), saturated 1:1 NaHCO3/Na2S2O4 (2×100 mL)
  7. dry with materialThe clear colorless ether layer was dried with sodium sulfate
  8. filtrationfiltered
  9. customevaporated in vacuo

出典と根拠

ORDレコード
ord-11ff55ee5aaf409f9418efb2833abb2a
出典データセット
uspto-grants-2004_04
特許番号
US06723716B1

反応ノート

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