Sodium hydride → N,N-dimethyl-2-chloro-5-[3,6-dihydro-4-trifluoromethyl-2,6-dioxo-1(2H)-pyrimidinyl]-benzenesulfonamide

HRID 1110148노트

반응식

HRID 1110148 반응식
[H-].[Na+].[NH2:3][C:4]([C:11]([F:14])([F:13])[F:12])=[CH:5][C:6]([O:8]CC)=O.[CH3:15][N:16]([CH3:30])[S:17]([C:20]1[CH:25]=[C:24]([N:26]=[C:27]=[O:28])[CH:23]=[CH:22][C:21]=1[Cl:29])(=[O:19])=[O:18]>O1CCCC1>[CH3:15][N:16]([CH3:30])[S:17]([C:20]1[CH:25]=[C:24]([N:26]2[C:6](=[O:8])[CH:5]=[C:4]([C:11]([F:12])([F:13])[F:14])[NH:3][C:27]2=[O:28])[CH:23]=[CH:22][C:21]=1[Cl:29])(=[O:19])=[O:18]

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 136209Ethyl 3-amino-4,4,4-trifluoro-2-butenoateHCID 18993674N,N-dimethyl-2-chloro-5-isocyanatobenzenesulfonamide

생성물 1

HCID 18993677N,N-dimethyl-2-chloro-5-[3,6-dihydro-4-trifluoromethyl-2,6-dioxo-1(2H)-pyrimidinyl]-benzenesulfonamide

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매3회

반응 조건

온도
-5 °C

실험 절차

To 30 ml of dried tetrahydrofuran (THF) cooled to -5° C. was added, under nitrogen, 3.6 g of sodium hydride as a 60% dispersion mineral oil. To the stirred slurry was added a solution of 10 g of ethyl 3-amino-4,4,4-trifluoro-2-butenoate in 30 ml of THF over a period of 30 minutes. After stirring at -5° C. for 1 hour, the reaction mixture was cooled to -65° C. and a solution of N, N-dimethyl-2-chloro-5-isocyanatobenzenesulfonamide (Example A-4 above) in 30 ml of THF was added dropwise maintaining the temperature below -60° C. The mixture was stirred at -65° C. for 2 hours and allowed to warm to room temperature. After stirring for 17 hours, solvent was removed using a rotary evaporator. About 50 ml of water was added to the residue. The resulting mixture was filtered to remove a small amount, of undissolved solid and the filtrate was acidified with hydrochloric acid. The resulting precipitate was filtered to give 13 g of the title compound as a beige solid, m.p. 281°-283° C.

후처리

  1. additionwas added, under nitrogen
  2. temperaturethe reaction mixture was cooled to -65° C.
  3. temperaturemaintaining the temperature below -60° C
  4. stirringThe mixture was stirred at -65° C. for 2 hours
  5. temperatureto warm to room temperature
  6. stirringAfter stirring for 17 hours
  7. customsolvent was removed
  8. customa rotary evaporator
  9. additionAbout 50 ml of water was added to the residue
  10. filtrationThe resulting mixture was filtered
  11. customto remove a small amount
  12. filtrationThe resulting precipitate was filtered

출처 및 근거

ORD 기록
ord-907f692af99d4b19b7910e1362187adc
출처 데이터셋
uspto-grants-1994_06
특허 번호
US05324854

반응 노트

불러오는 중…