Sodium hydride → 7-[1-(4-Trifluoromethylphenoxy)ethyl]-1,2,4-triazolo[1,5-a]pyrimidine

HRID 1290800노트

반응식

HRID 1290800 반응식
[F:1][C:2]([F:11])([F:10])[C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[CH:5][CH:4]=1.[H-].[Na+].Br[CH:15]([C:17]1[N:22]2[N:23]=[CH:24][N:25]=[C:21]2[N:20]=[CH:19][CH:18]=1)[CH3:16]>COCCOC>[F:1][C:2]([F:10])([F:11])[C:3]1[CH:4]=[CH:5][C:6]([O:9][CH:15]([C:17]2[N:22]3[N:23]=[CH:24][N:25]=[C:21]3[N:20]=[CH:19][CH:18]=2)[CH3:16])=[CH:7][CH:8]=1

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 678744-(Trifluoromethyl)phenolHCID 189193517-(1-Bromoethyl)-1,2,4-triazolo[1,5-a]pyrimidine

생성물 1

HCID 98395757-[1-(4-Trifluoromethylphenoxy)ethyl]-1,2,4-triazolo[1,5-a]pyrimidine

시약·촉매·용매 1

HCID 80711,2-Dimethoxyethane용매2회

실험 절차

4-Trifluoromethylphenol (1.62 g) was added to a stirred suspension of sodium hydride (0.48 g) in dry 1,2-dimethoxyethane (35 ml). The mixture was stirred at room temperature for 30 minutes, then a solution of 7-(1-bromoethyl)-1,2,4-triazolo[1,5-a]pyrimidine (2.27 g, prepared in a similar manner to that described in Example 6 below) in dry 1,2-dimethoxyethane (85 ml) was added dropwise. The mixture was stirred at room temperature for 24 hours. The sodium bromide was removed from the mixture by filtration. The solvent was evaporated from the filtrate and the residue dissolved in dichloromethane and washed with 200 ml of a 5% aqueous solution of sodium hydroxide followed by water. The organic layer was dried over magnesium sulphate. Evaporation of the solvent afforded a crude product which was purified by column chromatography on silica gel using as eluent a mixture of petroleum ether and ethyl acetate (in the ratio 6:4 respectively), followed by recrystallisation from hexane, to give 7-[1-(4-trifluoromethylphenoxy)ethyl]-1,2,4-triazolo[1,5-a]pyrimidine. Yield 1.1 g, (mp 100°-102° C.).

후처리

  1. additionwas added dropwise
  2. stirringThe mixture was stirred at room temperature for 24 hours
  3. customThe sodium bromide was removed from the mixture by filtration
  4. customThe solvent was evaporated from the filtrate
  5. dissolutionthe residue dissolved in dichloromethane
  6. washwashed with 200 ml of a 5% aqueous solution of sodium hydroxide
  7. dry with materialThe organic layer was dried over magnesium sulphate
  8. customEvaporation of the solvent
  9. customafforded a crude product which
  10. customwas purified by column chromatography on silica gel using as eluent
  11. additiona mixture of petroleum ether and ethyl acetate (in the ratio 6:4 respectively),
  12. customfollowed by recrystallisation from hexane

출처 및 근거

ORD 기록
ord-04009d33501e4c57ab782c08e16704d7
출처 데이터셋
uspto-grants-1998_05
특허 번호
US05753665

반응 노트

불러오는 중…