Methyl iodide → HCID 18436986, 화합물

HRID 2111723노트

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HRID 2111723 반응식
[CH2:1]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[C:15]3[S:21][CH:20]=[CH:19][C:16]=3[NH:17][N:18]=2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:22]C(C)([O-])C.[K+].CI.C([O-])(O)=O.[Na+]>C1COCC1>[CH2:1]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[C:15]3[S:21][CH:20]=[CH:19][C:16]=3[N:17]([CH3:22])[N:18]=2)[CH2:10][CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

6

반응물 4

HCID 6328Methyl iodideHCID 516892Sodium BicarbonateHCID 184369853-(4-benzyl-piperazin-1-yl)-1H-thieno[3,2-c]pyrazoleHCID 23665647Potassium tert-butoxide

생성물 1

HCID 18436986HCID 18436986, 화합물

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

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온도
-30 °C

실험 절차

To a stirred solution of 3-(4-benzyl-piperazin-1-yl)-1H-thieno[3,2-c]pyrazole (318.0 g, 1.07 mol) in THF (2.5 L) was added a mixture of potassium t-butoxide (134.4 g, 1.2 mol) in THF (1.5 L) dropwise over a period of 1 hour while keeping the reaction temperature below 25° C. After complete addition, the mixture was cooled to −30° C. and MeI (65.4 mL, 1.05 mol) was added dropwise over a period of 30 minutes. The mixture is then slowly warmed to room temperature overnight. To the reaction mixture is slowly added saturated NaHCO3 (1 L). The solution is then evaporated to remove the THF and the resulting aqueous mixture is taken up in EtOAc and washed with water and brine. The EtOAc extract is dried (Na2SO4), filtered and evaporated. The viscous concentrate is filtered through a silica gel plug with 1:1 EtOAc/heptane and evaporated yielding a viscous oil that is then dried under vacuum where it solidifies and yields 326.03 g (98%) as a 12:1 ratio of regioisomers in favor of the desired product.

후처리

  1. customthe reaction temperature below 25° C
  2. additionAfter complete addition
  3. temperatureThe mixture is then slowly warmed to room temperature overnight
  4. customThe solution is then evaporated
  5. customto remove the THF
  6. washwashed with water and brine
  7. extractionThe EtOAc extract
  8. dry with materialis dried (Na2SO4)
  9. filtrationfiltered
  10. customevaporated
  11. concentrationThe viscous concentrate
  12. filtrationis filtered through a silica gel plug with 1:1 EtOAc/heptane
  13. customevaporated
  14. customyielding a viscous oil that
  15. customis then dried under vacuum where it

출처 및 근거

ORD 기록
ord-ebf4cb5a7c064eb298cf66f5bb911d06
출처 데이터셋
uspto-grants-2009_04
특허 번호
US07521445B2

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