Sodium hydride → 7-{1-[4-(Ethylthio)phenoxy]ethyl}-1,2,4-triazolo[1,5-a]pyrimidine

HRID 1290808ノート

反応式

HRID 1290808 の反応式
[CH2:1]([S:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1)[CH3:2].[H-].[Na+].Br[CH:14]([C:16]1[N:21]2[N:22]=[CH:23][N:24]=[C:20]2[N:19]=[CH:18][CH:17]=1)[CH3:15]>COCCOC>[CH2:1]([S:3][C:4]1[CH:9]=[CH:8][C:7]([O:10][CH:14]([C:16]2[N:21]3[N:22]=[CH:23][N:24]=[C:20]3[N:19]=[CH:18][CH:17]=2)[CH3:15])=[CH:6][CH:5]=1)[CH3:2]

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 130853494-(Ethylthio)phenolHCID 189193517-(1-Bromoethyl)-1,2,4-triazolo[1,5-a]pyrimidine

生成物 1

HCID 97963597-{1-[4-(Ethylthio)phenoxy]ethyl}-1,2,4-triazolo[1,5-a]pyrimidine

試薬・触媒・溶媒 1

HCID 80711,2-Dimethoxyethane溶媒3 回

実験手順

A solution of 4-(ethylthio)phenol (1.54 g) in dry 1,2-dimethoxyethane was added slowly to a stirred suspension of sodium hydride (0.48 g) in dry 1,2-dimethoxyethane (35 ml). The mixture was stirred 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 above) in dry 1,2-dimethoxyethane (85 ml) was added dropwise. The reaction mixture was stirred overnight at room temperature. The sodium bromide was removed from the mixture by filtration. The solvent was evaporated from the mixture 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 diethylether and ethyl acetate (in the ratio 6:4 respectively), followed by recrystallisation from a mixture of ethyl acetate and hexane, to give 7-{1-[4-(ethylthio)phenoxy]ethyl}-1,2,4-triazolo[1,5-a]pyrimidine. Yield 2.28 g, (m.p. 65°-67° C.).

後処理

  1. additionwas added dropwise
  2. stirringThe reaction mixture was stirred overnight at room temperature
  3. customThe sodium bromide was removed from the mixture by filtration
  4. customThe solvent was evaporated from the mixture
  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 diethylether and ethyl acetate (in the ratio 6:4 respectively),
  12. customfollowed by recrystallisation from a mixture of ethyl acetate and hexane

出典と根拠

ORDレコード
ord-c5d39e04784c4739ba9e3899325066ab
出典データセット
uspto-grants-1998_05
特許番号
US05753665

反応ノート

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