3-Chloropropionic acid → HCID 17914321、化合物

HRID 1897727ノート

反応式

HRID 1897727 の反応式
[OH:1]/[N:2]=[C:3](/[NH2:7])\[CH:4]([CH3:6])[CH3:5].[Cl:8][CH2:9][CH2:10][C:11](O)=O.C1(N=C=NC2CCCCC2)CCCCC1>O1CCOCC1>[Cl:8][CH2:9][CH2:10][C:11]1[O:1][N:2]=[C:3]([CH:4]([CH3:6])[CH3:5])[N:7]=1

参加物

5

反応物 3

HCID 78993-Chloropropionic acidHCID 10868DicyclohexylcarbodiimideHCID 5712089N'-Hydroxy-2-methylpropanimidamide

生成物 1

HCID 17914321HCID 17914321、化合物

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

反応条件

温度
0 °C

実験手順

A mixture of (E)-N′-hydroxyisobutyrimidamide (510 mg, 5 mmol), 3-chloropropanoic acid (542 mg, 5 mmol) and dicyclohexylcarbodiimide (1.24 g, 6 mmol) in anhydrous dioxane (20 mL) was stirred at 0° C. for 1 h and then at room temperature for an additional 1 h. The reaction was then heated at 80° C. for an additional 18 h. The reaction was filtered and the filtrate was evaporated. The resulting residue was purified by silica chromatography (0-100% EtOAc in hexanes gradient) to give 5-(2-chloroethyl)-3-isopropyl-1,2,4-oxadiazole; 1H NMR (400 MHz, CDCl3) δ 3.85 (t, J=7.2 Hz, 2H), 3.27 (t, J=7.2 Hz, 2H), 3.03 (septet, J=7.2 Hz, 1H), 1.13 (d, J=7.2 Hz, 6H); ESMS m/z 175.1 (M+H+).

後処理

  1. waitat room temperature for an additional 1 h
  2. temperatureThe reaction was then heated at 80° C. for an additional 18 h
  3. filtrationThe reaction was filtered
  4. customthe filtrate was evaporated
  5. customThe resulting residue was purified by silica chromatography (0-100% EtOAc in hexanes gradient)

出典と根拠

ORDレコード
ord-d7ef070064064b09b1a946c769a985ec
出典データセット
uspto-grants-2013_08
特許番号
US08519129B2

反応ノート

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