Triethylamine → 5-(azidocarbonyl)-1-phenyl-1H-1,2,3-triazole

HRID 396284ノート

反応式

HRID 396284 の反応式
[C:1]1([N:7]2[C:11]([C:12]([OH:14])=O)=[CH:10][N:9]=[N:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.C(OC(Cl)=O)C.[N-:28]=[N+:29]=[N-:30].[Na+]>CC(C)=O.O>[N:28]([C:12]([C:11]1[N:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[N:8]=[N:9][CH:10]=1)=[O:14])=[N+:29]=[N-:30]

参加物

7

反応物 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 33557Sodium AzideHCID 28017501-phenyl-1H-1,2,3-triazole-5-carboxylic acid

生成物 1

HCID 230036295-(azidocarbonyl)-1-phenyl-1H-1,2,3-triazole収率 18%

試薬・触媒・溶媒 2

HCID 180Acetone溶媒HCID 962Water溶媒

反応条件

温度
0 °C

実験手順

To a solution of 1-phenyl-1H-1,2,3-triazole-5-carboxylic acid (500 mg, 2.64 mmol) in a mixture of acetone (10 mL) and water (5 mL) was added triethylamine (0.55 mL, 3.96 mmol). The mixture was cooled to 0° C. in a ice-bath. Ethylchloroformate (573 mg, 5.28 mmol) was then added and the resulting mixture was stirred for 1.5 hours at 0° C. To the mixture was added sodium azide (0.844 g, 13.0 mmol), and the mixture was stirred for another 1.5 hours. The mixture was concentrated, the residue was diluted with dichloromethane and washed with water. The organic layer was dried over MgSO4 and concentrated to give desired product (100 mg, 18%). 1HNMR (CDCl3) (δ) 8.30 (s, 1H), 7.57 (t, 3H), 7.51 (d, 2H).

後処理

  1. stirringthe mixture was stirred for another 1.5 hours
  2. concentrationThe mixture was concentrated
  3. additionthe residue was diluted with dichloromethane
  4. washwashed with water
  5. dry with materialThe organic layer was dried over MgSO4
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-c2dc63dbd1f9482691f9c88b43a0f34d
出典データセット
uspto-grants-2003_08
特許番号
US06608077B2

反応ノート

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