Triethylamine → 3-(Azidocarbonyl)-2-chloropyridine

HRID 396282ノート

反応式

HRID 396282 の反応式
[Cl:1][C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4](O)=[O:5].C(N(CC)CC)C.C(OC(Cl)=O)C.[N-:24]=[N+:25]=[N-:26].[Na+]>CC(C)=O.O>[N:24]([C:4]([C:3]1[C:2]([Cl:1])=[N:10][CH:9]=[CH:8][CH:7]=1)=[O:5])=[N+:25]=[N-:26]

参加物

7

反応物 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 33557Sodium AzideHCID 762582-Chloronicotinic acid

生成物 1

HCID 230036353-(Azidocarbonyl)-2-chloropyridine収率 48%

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 2-chloronicotinic acid (1.0 g, 6.35 mmol) in a mixture of acetone (14 mL) and water (6 mL) was added triethylamine (0.97 mL, 6.98 mmol). The mixture was cooled to 0° C. in a ice-bath. Ethylchloroformate (1.03 g, 9.5 mmol) was then added and the resulting mixture was stirred for 1.0 hour at 0° C. To the mixture was added sodium azide (0.70 g, 10.8 mmol), and the mixture was stirred for another 3 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 (550 mg, 48%). 1HNMR (CDCl3) (δ) 8.57 (d, 1H), 8.22 (d, 1H), 7.37 (t, 1H).

後処理

  1. stirringthe mixture was stirred for another 3 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-2c1c739b239049bca928398ae3b7e3dc
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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