Semicarbazide → 5-[(2-Chlorophenyl)methyl]-1,3,4-oxadiazol-2-amine

HRID 408485ノート

反応式

HRID 408485 の反応式
[NH2:1][NH:2][C:3]([NH2:5])=[O:4].[Cl:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[CH2:13][C:14](O)=O>P(Cl)(Cl)(Cl)=O>[Cl:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[CH2:13][C:14]1[O:4][C:3]([NH2:5])=[N:2][N:1]=1

参加物

4

反応物 2

HCID 5196SemicarbazideHCID 17124o-Chlorophenylacetic acid

生成物 1

HCID 180704165-[(2-Chlorophenyl)methyl]-1,3,4-oxadiazol-2-amine

試薬・触媒・溶媒 1

HCID 24813Phosphorus oxychloride溶媒

実験手順

Semicarbazide (9.0 g, 120 mmol) was slowly added to a solution of (2-chlorophenyl)acetic acid (10. g, 60 mmol) in phosphorus oxychloride (50 mL). The mixture was stirred at room temperature for 16 hours and then poured into crushed ice (500 g). A viscous solid was decanted from the aqueous layer and then the aqueous layer was adjusted to pH 4 to 5 with sodium hydroxide (50% aqueous solution). The resulting precipitate was filtered and then washed with sodium carbonate (10% aqueous solution, 100 mL) to give the product as a white solid. (5.9 g, 28 mmol, 47%). ESI-MS m/z calc. 209.0. found; 210.1 (M+1)+ 1H NMR (DMSO) δ 7.44-7.30 (m, 4H), 6.88 (s, 2H), 4.13 (s, 2H).

後処理

  1. additionpoured
  2. customA viscous solid was decanted from the aqueous layer
  3. filtrationThe resulting precipitate was filtered
  4. washwashed with sodium carbonate (10% aqueous solution, 100 mL)

出典と根拠

ORDレコード
ord-78f6e4b4c819463d94dc748a83eee5f9
出典データセット
uspto-grants-2014_06
特許番号
US08759335B2

反応ノート

読み込み中…