Ammonium Chloride → Rufinamide

HRID 335512ノート

反応式

HRID 335512 の反応式
C(Cl)(=O)C(Cl)=O.[F:7][C:8]1[CH:22]=[CH:21][CH:20]=[C:19]([F:23])[C:9]=1[CH2:10][N:11]1[CH:15]=[C:14]([C:16](O)=[O:17])[N:13]=[N:12]1.[Cl-].[NH4+:25].C(=O)(O)[O-].[Na+]>C1COCC1.O>[F:7][C:8]1[CH:22]=[CH:21][CH:20]=[C:19]([F:23])[C:9]=1[CH2:10][N:11]1[CH:15]=[C:14]([C:16]([NH2:25])=[O:17])[N:13]=[N:12]1

参加物

7

反応物 4

HCID 25517Ammonium ChlorideHCID 65578Oxalyl chloride2 回HCID 516892Sodium BicarbonateHCID 10014469Cgp-47292

生成物 1

HCID 129228Rufinamide収率 55.8%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
22.5 °C

実験手順

1.9 ml (22.4 mmol) of oxalyl chloride were added drop wise, to a suspension of 5 g (20.9 mmol) of 1-(2,6-difluorobenzyl)-1H-1,2,3-triazole-4-carboxylic acid in 12.5 ml of anhydrous THF, at 20-25° C. and under nitrogen atmosphere. Once the addition of oxalyl chloride was completed, the mixture was stirred at 20-25° C. for 4 h. Afterwards, the resulting mixture was concentrated under vacuum to dryness, in order to eliminate HCl and unreacted oxalyl chloride. The obtained residue was dissolved in ml of fresh anhydrous THF and treated with 4.0 g (75.2 mmol) of ammonium chloride and 5.26 g (62.7 mmol) of sodium bicarbonate over 16 h at 20-25° C. The resultant suspension was treated with 30 ml of water. The solid was filtrated and washed with 30 ml of a saturated aqueous sodium bicarbonate solution and twice with 30 ml of water. The solid was dried in a vacuum drier at 50° C. to yield 2.78 g (55.8%) of 1-(2,6-difluorobenzyl)-1H-1,2,3-triazole-4-carboxamide as Form R-5.

後処理

  1. customat 20-25° C.
  2. concentrationAfterwards, the resulting mixture was concentrated under vacuum to dryness, in order
  3. filtrationThe solid was filtrated
  4. washwashed with 30 ml of a saturated aqueous sodium bicarbonate solution and twice with 30 ml of water
  5. customThe solid was dried in a vacuum drier at 50° C.

出典と根拠

ORDレコード
ord-9045e347ccd5412a82438a066d2884db
出典データセット
uspto-grants-2014_11
特許番号
US08884026B2

反応ノート

読み込み中…