Dimethylamine → n,n-Dimethyl-5-(4-trifluoromethyl-3-pyridyl)-1,2,4-oxadiazole-3-carboxamide

HRID 47219노트

반응식

HRID 47219 반응식
[C:1](N1C=CN=C1)([N:3]1C=CN=[CH:4]1)=O.[F:13][C:14]([F:30])([F:29])[C:15]1[CH:20]=[CH:19][N:18]=[CH:17][C:16]=1[C:21]1[O:25][N:24]=[C:23]([C:26]([OH:28])=O)[N:22]=1.CNC>O1CCCC1>[CH3:1][N:3]([CH3:4])[C:26]([C:23]1[N:22]=[C:21]([C:16]2[CH:17]=[N:18][CH:19]=[CH:20][C:15]=2[C:14]([F:13])([F:30])[F:29])[O:25][N:24]=1)=[O:28]

참가 물질

5

반응물 3

HCID 674DimethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 227440715-(4-Trifluoromethyl-3-pyridyl)-1,2,4-oxadiazole-3-carboxylic acid

생성물 1

HCID 22744093n,n-Dimethyl-5-(4-trifluoromethyl-3-pyridyl)-1,2,4-oxadiazole-3-carboxamide

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

5.8 g of carbonyldiimidazole are initially charged in 90 ml of tetrahydrofuran and, a little at a time, admixed with 9 g of 5-(4-trifluoromethyl-3-pyridyl)-1,2,4-oxadiazole-3-carboxylic acid. The mixture is stirred at room temperature for 15 min and then heated at 50° C. for 2 h. After cooling to room temperature, 2.3 g of dimethylamine are introduced in a very gentle gas stream over a period of 2 h. After a reaction time of 12 h, the mixture is concentrated and taken up in 200 ml of diethyl ether. The mixture is washed with ice-cold half conc. hydrochloric acid solution, washed neutral with sat. sodium bicarbonate sol., dried over magnesium sulfate and concentrated under reduced pressure. This gives a slightly yellow oil which solidifies after a number of days to a solid of mp. 52-54° C.

후처리

  1. temperatureheated at 50° C. for 2 h
  2. temperatureAfter cooling to room temperature
  3. concentrationAfter a reaction time of 12 h, the mixture is concentrated
  4. washThe mixture is washed with ice-cold half conc. hydrochloric acid solution
  5. washwashed neutral with sat. sodium bicarbonate sol.
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThis gives a slightly yellow oil which

출처 및 근거

ORD 기록
ord-e29577b104444a7192a911f8cdd3ce8b
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06699853B2

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