Ammonium Chloride → Rufinamide

HRID 335512노트

반응식

HRID 335512 반응식
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

참가 물질

7

반응물 4

HCID 25517Ammonium ChlorideHCID 65578Oxalyl chloride2회HCID 516892Sodium BicarbonateHCID 10014469Cgp-47292

생성물 1

HCID 129228Rufinamide수율 55.8%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
22.5 °C

실험 절차

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.

후처리

  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.

출처 및 근거

ORD 기록
ord-9045e347ccd5412a82438a066d2884db
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08884026B2

반응 노트

불러오는 중…